Welcome to LookChem.com Sign In|Join Free

CAS

  • or

1125-88-8

Post Buying Request

1125-88-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

1125-88-8 Usage

Chemical Description

Different sources of media describe the Chemical Description of 1125-88-8 differently. You can refer to the following data:
1. Benzaldehyde dimethyl acetal is an organic compound used as a protecting group for aldehydes and ketones.
2. Benzaldehyde dimethyl acetal is a protecting group used to protect the hydroxyl groups of the carbohydrate molecule during the synthesis.
3. Benzaldehyde dimethyl acetal is a colorless liquid used as a protecting group for aldehydes and ketones.

Chemical Properties

Different sources of media describe the Chemical Properties of 1125-88-8 differently. You can refer to the following data:
1. Clear colorless liquid
2. Benzaldehyde dimethyl acetal has a sweet, floral note; also reminiscent of almond

Occurrence

Reported found in rhubarb and potato.

Uses

Different sources of media describe the Uses of 1125-88-8 differently. You can refer to the following data:
1. Benzaldehyde dimethyl acetal used as an effective reagent for the construction of selenocarbonyl compounds.
2. Benzaldehyde dimethyl acetal is suitable for use in the synthesis of 4,6-dihydroxy sugar, required for the total synthesis of Porphyromonas gingivalis 381 derived lipid A. It may be used in the preparation of 1-O-methyl-2,3-di-O-galloyl-β-D-glucose.
3. Benzaldehyde dimethyl acetal may be used as an analytical reference standard for the quantification of the analyte in fresh and canned fish and Cinnamomum zeylanicum using gas-chromatography coupled to mass spectrometry (GC-MS).

Preparation

Different sources of media describe the Preparation of 1125-88-8 differently. You can refer to the following data:
1. From benzaldehyde and methanol in the presence of calcium chloride and HCl; from benzaldehyde and tetramethylorthosilicate in the presence of anhydrous HCl in methanol
2. A mixture of ethylenediamine (1.2 g, 20 mmol), Ph3SbO (1.0 mmol), and P4S10 (2.0 mmol) was autoclaved under a pressure of CO2 (4.9 MPa). Imidazolidinone was isolated by column chromatography (silica gel; eluent: ethyl acetate/hexane, 1:1, v/v); yield 1.5 g (85%).

Taste threshold values

Taste characteristics at 25 ppm: green, nutty, brown and sweet

General Description

The abstraction of α-hydrogen atoms from benzaldehyde dimethyl acetal by active bromine at 80°C has been investigated.

Safety Profile

Moderately toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 1125-88-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 5 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1125-88:
(6*1)+(5*1)+(4*2)+(3*5)+(2*8)+(1*8)=58
58 % 10 = 8
So 1125-88-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O2/c1-10-9(11-2)8-6-4-3-5-7-8/h3-7,9H,1-2H3

1125-88-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B1197)  Benzaldehyde Dimethyl Acetal  >98.0%(GC)

  • 1125-88-8

  • 25mL

  • 140.00CNY

  • Detail
  • TCI America

  • (B1197)  Benzaldehyde Dimethyl Acetal  >98.0%(GC)

  • 1125-88-8

  • 100mL

  • 430.00CNY

  • Detail
  • TCI America

  • (B1197)  Benzaldehyde Dimethyl Acetal  >98.0%(GC)

  • 1125-88-8

  • 500mL

  • 1,230.00CNY

  • Detail
  • Alfa Aesar

  • (A11009)  Benzaldehyde dimethyl acetal, 99%   

  • 1125-88-8

  • 100g

  • 421.0CNY

  • Detail
  • Alfa Aesar

  • (A11009)  Benzaldehyde dimethyl acetal, 99%   

  • 1125-88-8

  • 500g

  • 1532.0CNY

  • Detail
  • Alfa Aesar

  • (A11009)  Benzaldehyde dimethyl acetal, 99%   

  • 1125-88-8

  • 2500g

  • 6513.0CNY

  • Detail
  • Aldrich

  • (226076)  Benzaldehydedimethylacetal  99%

  • 1125-88-8

  • 226076-100G

  • 452.79CNY

  • Detail
  • Aldrich

  • (226076)  Benzaldehydedimethylacetal  99%

  • 1125-88-8

  • 226076-500G

  • 1,751.49CNY

  • Detail
  • Aldrich

  • (381438)  Benzaldehydedimethylacetal  95%

  • 1125-88-8

  • 381438-100ML

  • 468.00CNY

  • Detail

1125-88-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzaldehyde dimethyl acetal

1.2 Other means of identification

Product number -
Other names α,α-Dimethoxytoluene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1125-88-8 SDS

1125-88-8Synthetic route

benzaldehyde
100-52-7

benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With [Sc2(C4O4)3]n In tetrachloromethane at 60℃; for 1h;100%
With lithium tetrafluoroborate In methanol for 0.5h; Heating;100%
indium(III) triflate In dichloromethane at 20℃; for 0.0833333h;99%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With trimethyl orthoformate at 20℃; for 0.5h;99%
With cobalt(II) 2-propyliminomethyl-phenolate functionalized mesoporous silica for 2h; Reflux;99%
With Zr6(µ3-O)4(µ3-OH)4(2,2-bis(trifluoromethyl)-4,4’-biphenyldicarboxylate)4[Cu(2,2'-bipyridine-5,5’-dicarboxylate)(MeCN)I](C6H3(NH-CO-C6H4-SO3H)(PhCOO)2) at 20℃; for 2h; Catalytic behavior; Reagent/catalyst;99%
methanol
67-56-1

methanol

3,3,5-triphenyl-1,2,4-trioxolane
23246-12-0

3,3,5-triphenyl-1,2,4-trioxolane

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzophenone
119-61-9

benzophenone

C

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With chlorosulfonic acid for 80h;A 75%
B 95%
C 25%
3,3,5-triphenyl-1,2,4-trioxolane
23246-12-0

3,3,5-triphenyl-1,2,4-trioxolane

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzophenone
119-61-9

benzophenone

C

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With chlorosulfonic acid In methanol for 80h;A 75%
B 95%
C 25%
methanol
67-56-1

methanol

toluene
108-88-3

toluene

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium perchlorate; Tris(2,4-dibromophenyl)amine In dichloromethane indirect electrochemical oxidation; Yields of byproduct given;A 95%
B n/a
C n/a
With lithium perchlorate direct electrochemical oxidation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methanol
67-56-1

methanol

3-chloro-3-phenyl-3H-diazirine
4460-46-2

3-chloro-3-phenyl-3H-diazirine

A

benzylidene dichloride
98-87-3

benzylidene dichloride

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
at 80℃; for 6h; Mechanism; other 3-chloro-3-aryldiazirines;A n/a
B 95%
C 1%
at 80℃; for 6h;A n/a
B 95%
C 1%
Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h; Product distribution;94%
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h;94%
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h;94%
In dichloromethane at -78℃; for 0.0833333h;
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With 2-Picolinic acid; ferrous(II) sulfate heptahydrate; dihydrogen peroxide at 20 - 60℃; for 12h; Schlenk technique; Molecular sieve;93%
With potassium trifluoroacetate at 55 - 60℃; electrochemical oxidation;42 % Spectr.
With tert.-butylhydroperoxide; C30H29ClN4ORu(2+)*2F6P(1-) at 50℃; Catalytic behavior; Kinetics; Reagent/catalyst; Schlenk technique; Molecular sieve;87 %Chromat.
With zinc indium sulfide; phenylmethanethiol for 15h; Irradiation;81 %Chromat.
methanol
67-56-1

methanol

1-propenylbenzene
873-66-5

1-propenylbenzene

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With 2-Picolinic acid; ferrous(II) sulfate heptahydrate; dihydrogen peroxide at 20 - 60℃; for 12h; Schlenk technique; Molecular sieve;93%
methanol
67-56-1

methanol

2-phenyl-1,3-oxathiolane
5721-88-0

2-phenyl-1,3-oxathiolane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With N-Bromosuccinimide at 20℃; for 0.166667h;92%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With oxygen; Pd5-Bi2-Pb1-Fe1/(100)SiO2-MgOA 90.3%
B n/a
With oxygen; Pd5-Bi2-Fe1/(100)SiO2-MgOA 88.8%
B n/a
With oxygen; Pd5-Bi2-Pb1-Co1/(100)SiO2A 88.6%
B n/a
methanol
67-56-1

methanol

3-α-bromobenzyloxy-3-fluorodiazirine
138173-30-5

3-α-bromobenzyloxy-3-fluorodiazirine

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism; also in the presence of HCl or bases, use of CD3OD/CD3CN, also with ethylene glycol or piperidine;90%
methanol
67-56-1

methanol

[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

benzaldehyde benzylidenehydrazone
28867-76-7

benzaldehyde benzylidenehydrazone

A

iodobenzene
591-50-4

iodobenzene

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With sodium methylate at 0 - 25℃; for 48h; Product distribution; Var. aldazines and alcohols;A n/a
B 88%
methanol
67-56-1

methanol

benzaldehyde benzylidenehydrazone
28867-76-7

benzaldehyde benzylidenehydrazone

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; sodium methylate at 0 - 25℃; for 48h;88%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
trimethylsilyl iodide In dichloromethane 1.) -78 deg C, 3 h, 2.) RT, 4h;87%
With hydrogenchloride
methanol
67-56-1

methanol

N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With bromine for 1h; Heating;87%
methanol
67-56-1

methanol

2-phenyl-1,3-dithiane
5616-55-7

2-phenyl-1,3-dithiane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With N-Bromosuccinimide at 20℃; for 0.0833333h;86%
trifluoroacetic acid-methyl ester
431-47-0

trifluoroacetic acid-methyl ester

sodium methylate
124-41-4

sodium methylate

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
In methanol at 20℃; Inert atmosphere;85%
methanol
67-56-1

methanol

chalcone epoxide
5411-12-1

chalcone epoxide

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

2-hydroxy-3-methoxy-1,3-diphenylpropan-1-one
412017-63-1

2-hydroxy-3-methoxy-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
With tetraethylammonium bromide at 25℃; Product distribution; reaction in CH3OD and nitromethane (1:50); in acetic acid; retention/inversion products;A 2%
B 13%
C 84%
benzaldehyde
100-52-7

benzaldehyde

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 70℃; Addition;84%
With toluene-4-sulfonic acid67%
methanol
67-56-1

methanol

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

1-phenyl-1,1,2-trimethoxyethane
143191-51-9

1-phenyl-1,1,2-trimethoxyethane

Conditions
ConditionsYield
With potassium fluoride; 100 mA cm-2 at 60℃; Product distribution; various supporting electrolytes and anode materials;A 82%
B 10%
With potassium fluoride at 60℃; 100 mA cm-2, Pt anode;A 82%
B 10%
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

C

1,4-dimethoxy-1,4-diphenylbutane
32673-77-1

1,4-dimethoxy-1,4-diphenylbutane

D

1-phenyl-1,2,2-trimethoxy ethane
54845-42-0

1-phenyl-1,2,2-trimethoxy ethane

Conditions
ConditionsYield
With potassium fluoride at 60℃; 100 mA cm-2, Pt anode; Further byproducts given;A 1%
B 80%
C 3%
D 5%
With TPC at 60℃; 100 mA cm-2, C anode;A 16%
B 45%
C 13%
D 2%
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

C

1,4-dimethoxy-1,4-diphenylbutane
32673-77-1

1,4-dimethoxy-1,4-diphenylbutane

D

1-phenyl-1,2,2-trimethoxy ethane
54845-42-0

1-phenyl-1,2,2-trimethoxy ethane

E

meso-1,4-dimethoxy-2,3-diphenylbutane
80621-69-8

meso-1,4-dimethoxy-2,3-diphenylbutane

F

1,4-dimethoxy-1,3-diphenylbutane
80634-49-7

1,4-dimethoxy-1,3-diphenylbutane

Conditions
ConditionsYield
With potassium fluoride; 100 mA cm-2 at 60℃; Product distribution; various supporting electrolytes and anode materials;A 1%
B 80%
C 3%
D 5%
E 2%
F 2%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

acetophenone
98-86-2

acetophenone

A

acetophenone dimethyl acetal
4316-35-2

acetophenone dimethyl acetal

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With CoCl2 for 2h; Heating;A n/a
B 77%
benzylidene dichloride
98-87-3

benzylidene dichloride

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
at 225℃; for 39h;76%
With zinc(II) chloride at 20 - 25℃; for 1h;
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With Eco1a; dihydrogen peroxide In water at 20℃; for 17h; Reflux;A 76%
B 10%
C 11%
With dihydrogen peroxide; zinc(II) chloride In water at 20℃;
With oxygen at 179.84℃; under 7500.75 Torr; for 2h; Inert atmosphere;
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C29H25Cl2N4Ru(1+)*F6P(1-) at 50℃; for 6h; Reagent/catalyst; Schlenk technique; Molecular sieve;A 73%
B 7%
With ozone; thiourea 1) -10-(-15) deg C, 65 min, CH3OH; 2) 0 deg C, 55 min; Yield given. Multistep reaction;
α-chlorobenzyl methyl ether
35364-99-9

α-chlorobenzyl methyl ether

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
at 20℃; for 24h;72%
α-chlorobenzyl methyl ether
35364-99-9

α-chlorobenzyl methyl ether

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

Methyl formate
107-31-3

Methyl formate

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
A n/a
B 72%
methanol
67-56-1

methanol

Cyclohepta-1,3,5-triene
544-25-2

Cyclohepta-1,3,5-triene

A

7-methoxy-1,3,5-cycloheptatriene
1714-38-1

7-methoxy-1,3,5-cycloheptatriene

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With sodium methylate; tetraethylammonium tosylate at -10 - 0℃; anodic oxidation;A 71%
B 15%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

4-methoxy-4-phenyl-1-butene
22039-97-0

4-methoxy-4-phenyl-1-butene

Conditions
ConditionsYield
With trimethylaluminum; aluminum tri-bromide; copper(I) bromide In dichloromethane; toluene at 20℃; for 3h;100%
With 2,4-dinitrobenzenesulfonic acid In acetonitrile at 20℃; for 1h; Hosomi-Sakurai reaction;99%
With 30% bis[triphenyl(3-sulfopropyl)phosphonium]HPW12O40/SiO2 In acetonitrile at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent; Hosomi-Sakurai Reaction; Inert atmosphere; Green chemistry; chemoselective reaction;99%
4-methoxy-5H-furan-2-one
69556-70-3

4-methoxy-5H-furan-2-one

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

methyl 5-(1-methoxybenzyl)tetronate
82204-21-5

methyl 5-(1-methoxybenzyl)tetronate

Conditions
ConditionsYield
zinc dibromide100%
With n-butyllithium; boron trifluoride diethyl etherate 1.) ether, hexane, -78 deg C, 2.) ether, -78 deg C.; Yield given. Multistep reaction;
1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

3-methoxy-1,3-diphenylpropan-1-one
89524-37-8

3-methoxy-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
polymeric dicyanoketene acetal In acetonitrile for 6.5h; Substitution; Heating;100%
With polymer-supported DCKA In acetonitrile for 6.5h; Heating;100%
With Celite; polystyrene-bound super Broensted acid In toluene at 20℃; flow system;99%
1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

Conditions
ConditionsYield
With chloromethyl methyl ether; tin(ll) chloride In dichloromethane for 2h; Ambient temperature;100%
1-(Trimethylsilyloxy)cyclohexene
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(E)-2-benzylidenecyclohexanone
5682-83-7, 31021-02-0, 1467-15-8

(E)-2-benzylidenecyclohexanone

Conditions
ConditionsYield
With acetyl chloride; tin(ll) chloride In dichloromethane for 2h; Product distribution; Ambient temperature; effect of catalyst-activator system;100%
With acetyl chloride; tin(ll) chloride In dichloromethane for 2h; Ambient temperature;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

tributyltin phenyl sulfide
17314-33-9

tributyltin phenyl sulfide

(methoxy(phenylthio))methylbenzene
13865-07-1

(methoxy(phenylthio))methylbenzene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In hexane; toluene addn. of BF3*OEt2 in toluene to the acetal in toluene at -78°C and stirring for 1 h; GLC analysis;100%
With boron trifluoride diethyl etherate In hexane; toluene at -78℃; for 1h;100 % Chromat.
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

2-methoxy-2-phenylacetonitrile
13031-13-5

2-methoxy-2-phenylacetonitrile

Conditions
ConditionsYield
With titanium tetrachloride at -78 - -30℃;100%
With titanium tetrachloride In dichloromethane at -70 - 20℃; for 3h;96%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 0.0833333h;100%
With water at 80℃; for 2h;100%
With water at 90℃; Inert atmosphere;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol
2936-70-1, 5624-48-6, 13992-15-9, 16758-34-2, 28244-97-5, 77481-62-0, 77481-63-1, 105088-17-3, 149495-84-1

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
71676-30-7, 87508-18-7, 138922-03-9, 87508-17-6

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; pH=2 - 3; Inert atmosphere;100%
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 60℃; for 0.166667h; Sonication; Inert atmosphere; regioselective reaction;95%
With iron(III) chloride In acetonitrile at 20℃; for 2.5h; regioselective reaction;92%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

5,5-dimethyl-2-phenyl-[1,3]dioxane
776-88-5

5,5-dimethyl-2-phenyl-[1,3]dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane Inert atmosphere;100%
With 4 A molecular sieve; camphor-10-sulfonic acid In dichloromethane for 0.5h;99%
With camphor-10-sulfonic acid In dichloromethane Ambient temperature;97%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,4R,5R)-5-Methyl-hept-6-ene-2,4-diol
163380-63-0

(2R,4R,5R)-5-Methyl-hept-6-ene-2,4-diol

(4R,6R)-4-Methyl-6-((R)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

(4R,6R)-4-Methyl-6-((R)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 25℃; for 1.5h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,4S,5S)-5-Methyl-hept-6-ene-2,4-diol
155581-30-9

(2R,4S,5S)-5-Methyl-hept-6-ene-2,4-diol

(4R,6S)-4-Methyl-6-((S)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

(4R,6S)-4-Methyl-6-((S)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 25℃; for 1.5h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(Z)-(1R,4S,7R,8R)-3-Allyl-4,8-bis-benzyloxy-7-methoxymethoxy-2,2-dimethyl-cyclooct-5-ene-1,3-diol

(Z)-(1R,4S,7R,8R)-3-Allyl-4,8-bis-benzyloxy-7-methoxymethoxy-2,2-dimethyl-cyclooct-5-ene-1,3-diol

(Z)-(1S,2S,5R,6S,7R,9S)-1-Allyl-2,6-bis-benzyloxy-5-methoxymethoxy-11,11-dimethyl-9-phenyl-8,10-dioxa-bicyclo[5.3.1]undec-3-ene

(Z)-(1S,2S,5R,6S,7R,9S)-1-Allyl-2,6-bis-benzyloxy-5-methoxymethoxy-11,11-dimethyl-9-phenyl-8,10-dioxa-bicyclo[5.3.1]undec-3-ene

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

methyl beta-D-glucopyranoside
709-50-2

methyl beta-D-glucopyranoside

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
71117-37-8

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 37.5038 Torr; for 2h;100%
With (1S)-10-camphorsulfonic acid In acetonitrile at 20℃; for 4h;93%
With iodine In acetonitrile at 20℃; for 1h;92%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

methyl α-D-galactopyranoside
3396-99-4

methyl α-D-galactopyranoside

methyl 4,6-O-benzylidene-α-D-galactopyranoside
64552-06-3

methyl 4,6-O-benzylidene-α-D-galactopyranoside

Conditions
ConditionsYield
With camphor-10-sulfonic acid In chloroform at 65℃;100%
With tetrafluoroboric acid In diethyl ether; N,N-dimethyl-formamide at 20℃; for 16h;96%
With toluene-4-sulfonic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 2h;92%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester
182865-98-1

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester

((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester
182865-71-0

((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile100%
methanol
67-56-1

methanol

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With carbon tetrabromide; oxygen for 5h; Irradiation;100%
With hydrogenchloride; dihydrogen peroxide95%
With dihydrogen peroxide In water at 30℃; for 3h; Green chemistry;65%
With oxygen at 90℃; under 3800.26 Torr; for 2h;
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

tetraallyl tin
7393-43-3

tetraallyl tin

1-Phenyl-3-buten-1-ol
80735-94-0

1-Phenyl-3-buten-1-ol

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol at 30℃; for 20h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(Z)-1-Trimethylsilanyl-5-trimethylsilanyloxy-pent-2-ene
193829-28-6

(Z)-1-Trimethylsilanyl-5-trimethylsilanyloxy-pent-2-ene

(2R,3R)-2-Phenyl-3-vinyl-tetrahydro-furan

(2R,3R)-2-Phenyl-3-vinyl-tetrahydro-furan

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -20℃; for 0.333333h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With camphor-10-sulfonic acid In acetonitrile at 20℃; for 12h;100%
With camphor-10-sulfonic acid In acetonitrile at 20℃; regioselective reaction;93%
With toluene-4-sulfonic acid In acetonitrile for 2h; Ambient temperature; Yield given;
With camphor-10-sulfonic acid In acetonitrile at 20℃;
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,3S,4R)-3-Benzyloxy-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-1,1-bis-ethylsulfanyl-pentane-2,4-diol
199850-99-2

(2R,3S,4R)-3-Benzyloxy-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-1,1-bis-ethylsulfanyl-pentane-2,4-diol

{4-[(2R,4R,5S,6R)-5-Benzyloxy-6-(bis-ethylsulfanyl-methyl)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2,6-dimethoxy-phenoxy}-tert-butyl-dimethyl-silane

{4-[(2R,4R,5S,6R)-5-Benzyloxy-6-(bis-ethylsulfanyl-methyl)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2,6-dimethoxy-phenoxy}-tert-butyl-dimethyl-silane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene for 0.333333h; Ambient temperature;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,3R,4S,5S,6R)-2-Dicyclohexylmethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
197164-63-9

(2R,3R,4S,5S,6R)-2-Dicyclohexylmethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

(2R,4aR,6R,7R,8R,8aS)-6-Dicyclohexylmethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
197164-99-1

(2R,4aR,6R,7R,8R,8aS)-6-Dicyclohexylmethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 57℃; under 20 Torr; for 3h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

N-(2-hydroxycyclohexyl)-4-methylbenzenesulfonamide
58107-40-7, 69291-83-4

N-(2-hydroxycyclohexyl)-4-methylbenzenesulfonamide

(3aR,7aS)-2-Phenyl-3-(toluene-4-sulfonyl)-octahydro-benzooxazole

(3aR,7aS)-2-Phenyl-3-(toluene-4-sulfonyl)-octahydro-benzooxazole

Conditions
ConditionsYield
With 4 A molecular sieve; pyridinium p-toluenesulfonate In toluene for 48h; Heating;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

trans-2-(tert-butylamino)cyclohexan-1-ol
55915-78-1, 65760-72-7, 109735-34-4, 131164-09-5

trans-2-(tert-butylamino)cyclohexan-1-ol

(3a,7a-trans)-octahydro-3-(t-butyl)-2-phenylbenzoxazole

(3a,7a-trans)-octahydro-3-(t-butyl)-2-phenylbenzoxazole

Conditions
ConditionsYield
With 4 Angstroem molecular sives; pyridinium p-toluenesulfonate In toluene for 100h; Heating;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

phenyl-β-D-glucopyranoside
1464-44-4

phenyl-β-D-glucopyranoside

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 12h;100%
With sodium hydrogen sulfate; silica gel In acetonitrile at 20℃; for 4h;95%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 0℃; for 48h;95%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

acetophenone
98-86-2

acetophenone

tributyl-(1-ethoxy-vinyloxy)-silane

tributyl-(1-ethoxy-vinyloxy)-silane

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

A

4-methoxy-4-phenyl-1-butene
22039-97-0

4-methoxy-4-phenyl-1-butene

B

3-phenyl-3-tributylsilanyloxy-butyric acid ethyl ester

3-phenyl-3-tributylsilanyloxy-butyric acid ethyl ester

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 9h; parallel recognition;A 100%
B 95%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate
220384-85-0

ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate
220384-86-1

ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene for 1h; Heating;100%
With camphor-10-sulfonic acid In benzene for 1h; Cyclization; Heating;95%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine
316804-46-3

6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine
316804-47-4

6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; under 35 Torr; for 1h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate
212136-31-7

ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate

(2S,4R,5R)-5-Methyl-5-methylsulfanyl-2,4-diphenyl-[1,3]dioxane

(2S,4R,5R)-5-Methyl-5-methylsulfanyl-2,4-diphenyl-[1,3]dioxane

Conditions
ConditionsYield
Stage #1: ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate With lithium borohydride In dichloromethane at 20℃;
Stage #2: benzaldehyde dimethyl acetal With camphor-10-sulfonic acid In dichloromethane at 20℃;
100%

1125-88-8Relevant articles and documents

Hydrothermal synthesis of chiral inorganic-organic CoII complex: Structural, thermal and catalytic evaluation

Salah, Assila Maatar Ben,Herrera, Raquel P.,Na?li, Houcine

, p. 356 - 362 (2018)

By heating the cobalt chloride hexahydrate (CoCl2·6H2O) with the R form of the organic amine α-methylbenzylamine (C8H11N) under hydro(solvo)thermal conditions, we have successfully generated the corresponding non-centrosymmetric homochiral hybrid tris (α-methylbenzylammonium tetrachloridocobaltate chloride [R-(C8H12N)3][CoCl4]Cl abbreviated R(MBA)Co. We present the growth conditions together with a characterization of the single crystals by means of X-ray single-crystal diffraction, Fourier-transform infrared, TG/TDA thermal decomposition and catalytic properties. This inorganic–organic hybrid compound crystallizes in the chiral space group P21 and exhibits a supramolecular-layered organization wherein a double layer of (R)-methylbenzylammonium cations and the uncoordinated chloride anions are sandwiched between anionic layers, formed by isolated tetrachloridocobaltate tetrahedra. The crystal packing is governed by a three-dimensional network of N/C–H?Cl hydrogen bonds between the inorganic and organic moieties and C–H···π interactions between the aromatic rings of the organic moieties themselves. Thermal analysis discloses a phase transition at the temperature 130 °C. The Co complex was also employed as suitable catalyst activating the acetal formation reaction of aldehydes using MeOH as solvent and as the unique source of acetalization.

Ru(II)-functionalized SBA-15 as highly chemoselective, acid free and sustainable heterogeneous catalyst for acetalization of aldehydes and ketones

Lazar, Anish,Betsy,Vinod,Singh

, p. 62 - 66 (2018)

Combining electron deficient Ru(II) coordination sites with organofunctionalized SBA-15, (L)Ru(II)@SBA-15, result in a mild, neutral, water scavenger free and chemo-selective acetalization catalyst for cyclic/acyclic acetals. Vacant coordination sites of ruthenium in (L)Ru(II)@SBA-15 activates protecting groups as well as reactants simultaneously and restricts the reverse acetalization reaction. Synthesized (L)Ru(II)@SBA-15 catalyst has been thoroughly characterized and act as competitive catalyst compared to conventional acid catalysts. (L)Ru(II)@SBA-15 performs high catalytic activity as well as selectivity within 20 min with high TOF. The catalyst can be recycled and reaction parameters are optimized.

Direct Asymmetric Friedel-Crafts Reaction of Naphthols with Acetals Catalyzed by Chiral Bronsted Acids

Qin, Long,Wang, Pei,Zhang, Yixin,Ren, Zhengxiang,Zhang, Xin,Da, Chao-Shan

, p. 571 - 574 (2016)

The Friedel-Crafts method synthesis of chiral ethers from various acetals and naphthols catalyzed by chiral Bronsted acids with acetic acid as an effective additive is described. We found that the chiral phosphoric acid (R)-TRIP could efficiently catalyze the asymmetric Friedel-Crafts reaction of naphthols with acetals affording chiral ethers in good enantioselectivity and yield.

Crystallisation, thermal analysis and acetal protection activity of new layered Zn(II) hybrid polymorphs

Sa?d, Salem,Na?li, Houcine,Bataille, Thierry,Herrera, Raquel P.

, p. 5365 - 5374 (2016)

Two new polymorphic mononuclear complexes, with analogous structural formula (C6H9N2)2[Zn(H2O)6](SO4)2·2H2O, of zinc(ii) templated by 2-amino-6-methylpyridinium ligand have been discovered. These polymorphic hybrid crystals, which differ only in terms of their crystal structures, were prepared in one-step synthesis under ambient conditions and investigated for their thermal and catalytic properties. Single-crystal X-ray diffraction of the obtained materials revealed that polymorphs 1 and 2 crystallise in the triclinic system, space group P1. In an effort to further explore the form diversity of these compounds, the structural arrangements and intermolecular interactions such as hydrogen-bonding and π?π interactions are discussed from which supramolecular assembly was formed. Meanwhile, these new polymorphic forms can be described as the stacking of 3D layers where the interlayer distances are 13.23 and 12.59 ? for 1 and 2, respectively. The thermal behaviour of the precursors checked by TG-DTA analysis for both zinc sulfate polymorphs and variable temperature powder X-ray diffraction (VT-PXRD) show successive intermediate crystalline anhydrous phases upon dehydration in 1. The catalytic activity of both polymorphic structures has been tested in the acetalisation reaction of aldehydes as a benchmark process. Interestingly, both complexes showed excellent activity with almost total conversion in many examples and using MeOH as solvent and as the unique source of acetalisation.

MOF-808 as a recyclable catalyst for the photothermal acetalization of aromatic aldehydes

Rabon, Allison M.,Doremus, Jared G.,Young, Michael C.

, (2021)

Metal-organic frameworks (MOFs) show promise for catalysis applications due to their porosity, high internal surface area, and structural adaptability. Typical acetylation reactions of aldehydes require elevated temperatures and excess alcohol to drive the reactions to completion. In this current work, MOF-808 is used as a heterogeneous catalyst for acetylation of aldehydes in methanol using a mild photothermal process. Optimized conditions gave 72% yield of 2-(dimethoxymethyl)naphthalene in the presence of 10 mol% MOF-808 at 45 °C using only a fluorescent lamp. MOF-808 can be recycled up to 5 times with no loss in catalytic activity. A proof-of-principle substrate scope demonstrates the potential utility for aromatic and aliphatic substrates.

Davis et al.

, p. 2349 (1976)

Modification of Au nanoparticles electronic state by MOFs defect engineering to realize highly active photocatalytic oxidative esterification of benzyl alcohol with methanol

Fan, Chaoyang,Wang, Ruiyi,Kong, Peng,Wang, Xiaoyu,Wang, Jie,Zhang, Xiaochao,Zheng, Zhanfeng

, (2020)

Defect modified UiO-66 supported Au nanoparticles exhibited excellent catalytic performance in the oxidative esterification of benzyl alcohol with methanol under mild conditions. The defects were generated by introducing HCl during the preparation procedure. The defects exposed the Lewis acid of coordinatively unsaturated metal sites, which is benefit for Au loading and changing Au nanoparticles (NPs) to a negative electron state. The negatively charged Au nanoparticle promoted the reaction by strong oxygen activation ability. The present study could help to unravel the synergistic effect of support and metal interaction and provides an efficient photocatalytic route for synthesis high-value esters in terms of sustainable chemistry.

Electrochemical methoxylation of styrene with gas-lift in continuous mode

Il'chibaeva,Kagan,Tomilov

, p. 1318 - 1320 (2001)

Anodic oxidation of styrene in methanol was performed in an electrolyzer with gas-lift. The possibility of carrying this process out in continuous mode with the use of technical-grade methanol was studied.

New reaction of di- and trichloromethylbenzenes with orthoformic esters [6]

Gazizov,Gazizov,Karimova,Pudovik,Nikitin,Sinyashin

, p. 1465 - 1466 (2004)

-

Series of 2D heterometallic coordination polymers based on ruthenium(III) oxalate building units: Synthesis, structure, and catalytic and magnetic properties

Dikhtiarenko, Alla,Khainakov, Sergei A.,De Pedro, Imanol,Blanco, Jesus A.,Garcia, Jose R.,Gimeno, Jose

, p. 3933 - 3941 (2013)

A series of 2D ruthenium-based coordination polymers with hcb-hexagonal topology, {[K(18-crown-6)]3[MII3(H 2O)4{Ru(ox)3}3]}n (M II = Mn (1), Fe (2), Co (3), Cu (4), Zn (5)), has been synthesized through self-assembly reaction. All compounds are isostructural frameworks that crystallize in the monoclinic space group C2/c. The crystal packing consists of a 2D honeycomb-like anionic mixed-metal framework intercalated by [K(18-crown-6)]+ cationic template. Dehydration processes take place in the range 40-200 C exhibiting two phase transitions. However, the spontaneous rehydration occurs at room temperature. Both hydrated and dehydrated compounds were tested as Lewis acids heterogeneous catalysts in the acetalyzation of benzaldehyde achieving high yields with the possibility to be recovered and reused. All the investigated materials do not show any long-range magnetic ordering down to 2 K. However, the Fe-based compound 2 presents a magnetic irreversibility in the ZFC-FC magnetization data below 5 K, which suggest a spin-glass-like behavior, characterized also by short-range ferromagnetic correlations. The coercive field increases as the temperature is lowered below 5 K, reaching a value of 1 kOe at 2 K. Alternating current measurements obtained at different frequencies confirm the freezing process that shows weak frequency dependence, being characteristic of a system exhibiting competing magnetic interactions.

Cobalt(II) schiff base functionalized mesoporous silica as an efficient and recyclable chemoselective acetalization catalyst

Rajabi

, p. 695 - 701 (2010)

Cobalt(II) Schiff base functionalized mesoporous silica was synthesized from covalent attachment via the introduction of Co(OAc)2 to salicylaldimine functionalized mesoporous silica. The catalyst proved to be chemoselective one for the acetalization of aldehydes to the corresponding acetals in alcohol. The immobilized catalyst can be easily recovered and reused for at least ten reaction cycles without significant loss of its catalytic activity.

A new molecular iodine-catalyzed acetalization of carbonyl compounds

Basu, Manas K.,Samajdar, Susanta,Becker, Frederick F.,Banik, Bimal K.

, p. 319 - 321 (2002)

A new and facile molecular iodine-catalyzed acetalization of carbonyl compounds has been developed. Useful selectivity has also been demonstrated.

Influence of Terephthalic Acid Substituents on the Catalytic Activity of MIL-101(Cr) in Three Lewis Acid Catalyzed Reactions

Santiago-Portillo, Andrea,Navalón, Sergio,Concepción, Patricia,álvaro, Mercedes,García, Hermenegildo

, p. 2506 - 2511 (2017)

Six isostructural MIL-101(Cr)-X (X: H, NO2, SO3H, Cl, CH3, and NH2) materials have been prepared directly by the reaction of CrIII salts and the corresponding terephthalic acid or by postsynthetic treatments of preformed MIL-101(Cr) following reported procedures. The materials were characterized by using XRD (crystallinity and coincident diffraction pattern), isothermal N2 adsorption (specific surface areas range from 2740 m2 g?1 for MIL-101(Cr)-H to 1250 m2 g?1 for MIL-101(Cr)-Cl), thermogravimetry (thermal stability up to 400 °C), and IR spectroscopy (detection of the corresponding substituents), and the results were all in agreement with the reported data for these materials. The MIL-101(Cr) materials were tested as heterogeneous catalysts for epoxide ring opening by methanol, benzaldehyde acetalization by methanol, and Prins coupling, observing a clear influence of the substituent that in general follows a linear relationship with the Hammett σmeta constant of the substituent: the catalytic activity increases as the electron-withdrawing ability of the substituents increases. An up to three orders of magnitude enhancement in the presence of the NO2 substituent was found for some of these reactions. The present study illustrates the versatility that metal–organic frameworks offer as heterogeneous catalysts that allow the design of actives sites with adequate properties tuned for each reaction.

Guest molecule release triggers changes in the catalytic and magnetic properties of a FeII-based 3D metal-organic framework

Xu, Zhouqing,Meng, Wei,Li, Huijun,Hou, Hongwei,Fan, Yaoting

, p. 3260 - 3262 (2014)

A FeII-based metal-organic framework (MOF), {[Fe 2(pbt)2(H2O)2]·2H 2O}n, undergoes an irreversible dehydration, which triggers changes in the catalytic and magnetic properties of the MOF. These property changes are attributed to the high-spin to low-spin transition of 7.1% center FeII, which is demonstrated by 57Fe Moessbauer, X-ray photoelectron spectroscopy, and UV/vis absorption spectra.

Hierarchical porous organic polymer as an efficient metal-free catalyst for acetalization of carbonyl compounds with alcohols

Kim, Joong-Jo,Lim, Cheang-Rae,Reddy, Benjaram M.,Park, Sang-Eon

, p. 43 - 50 (2018)

An efficient melamine-porous organic polymer (M-POP) as N-functionalized organic polymer catalyst was synthesized with melamine and terephthalaldehyde by a facile microwave-assisted method. The synthesized M-POP exhibited a high specific surface area with hierarchical pore structure of both mesoporosity and microporosity. The rich N-moieties namely, C[dbnd]N and N–H from the melamine precursor were found to show hydrogen-bonding ability with various organic molecules such as carbonyl compounds. This was illustrated in the acetalization of aldehydes and ketones with methanol or ethylene glycol under mild conditions as a metal-free H-bonding catalyst with high product selectivity. The superior catalytic performance of M-POP was attributed to the availability of a large number of H-bonding sites both as H-donor and H-acceptor between the reactants and the catalyst.

A novel, mesoporous molybdenum doped titanium dioxide/reduced graphene oxide composite as a green, highly efficient solid acid catalyst for acetalization

He, Junkai,Kankanam Kapuge, Tharindu,Kerns, Peter,Meguerdichian, Andrew G.,Suib, Steven L.,Thalgaspitiya, Wimalika R. K.

, p. 3786 - 3795 (2020)

A novel, mesoporous composite of Mo doped TiO2/reduced graphene oxide is synthesized to be used as a highly efficient heterogeneous acid catalyst. The composite has a high surface area (263 m2 g-1) and a monomodal pore size distribution with an average pore diameter of 3.4 nm. A comprehensive characterization of the synthesized material was done using PXRD, Raman, BET, SEM, EDX, TEM, TGA, and XPS. The composite exhibited excellent catalytic activity (1.6 h-1 TOF, >99% GC yield, and >99% selectivity) towards acetalization of cyclohexanone at room tempertaure within 30 minutes. The catalyst was reusable up to 4 reaction cycles without any significant loss in the activity and the acidic site calculations showed that the reaction is mostly driven by the weak acidic sites on the composite.

The use of anhydrous CeCl3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones

Silveira, Claudio C.,Mendes, Samuel R.,Ziembowicz, Francieli I.,Lenarda?o, Eder J.,Perin, Gelson

, p. 371 - 374 (2010)

An efficient, clean, chemoselective and solvent-free method for the synthesis of ketone and aldehyde dimethyl acetals was developed using trimethyl orthoformate and commercially available anhydrous CeCl3 as a recyclable catalyst. The method is general and affords the protected carbonyl compounds in good yields and under mild conditions, including aryl and alkyl ketones and activated aldehydes. The catalyst could be utilised directly for 3 cycles, without significant loss of activity.

Robust Multifunctional Yttrium-Based Metal-Organic Frameworks with Breathing Effect

Firmino, Ana D. G.,Mendes, Ricardo F.,Antunes, Margarida M.,Barbosa, Paula C.,Vilela, Sérgio M. F.,Valente, Anabela A.,Figueiredo, Filipe M. L.,Tomé, Jo?o P. C.,Paz, Filipe A. Almeida

, p. 1193 - 1208 (2017)

Phosphonate- and yttrium-based metal-organic frameworks (MOFs), formulated as [Y(H5btp)]·5.5H2O (1), [Y(H5btp)]·2.5H2O (2), (H3O)[Y2(H5btp)(H4btp)]·H2O (3), and [Y(H5btp)]·H2O·0.5(MeOH) (4), were prepared using a “green” microwave-assisted synthesis methodology which promoted the self-assembly of the tetraphosphonic organic linker [1,1′-biphenyl]-3,3′,5,5′-tetrayltetrakis(phosphonic acid) (H8btp) with Y3+ cations. This new family of functional materials, isolated in bulk quantities, exhibits a remarkable breathing effect. Structural flexibility was thoroughly studied by means of X-ray crystallography, thermogravimetry, variable-temperature X-ray diffraction, and dehydration and rehydration processes, ultimately evidencing a remarkable reversible single-crystal to single-crystal (SC-SC) transformation solely through the loss and gain of crystallization solvent molecules. Topologically, frameworks remained unaltered throughout this interconversion mechanism, with all compounds being binodal 6,6-connected network with a Scha?fli symbol of {413.62}{48.66.8}. Results show that this is one of the most stable and thermally robust families of tetraphosphonate-based MOFs synthesized reported to date. Porous materials 2 and 3 were further studied to ascertain their performance as heterogeneous catalysts and proton conductors, respectively, with outstanding results being registered for both materials. Compound 2 showed a 94% conversion of benzaldehyde into (dimethoxymethyl)benzene after just 1 h of reaction, among the best results registered to date for MOF materials. On the other hand, the protonic conductivity of compound 3 at 98% of relative humidity (2.58 × 10-2 S cm-1) was among the highest registered among MOFs, with the great advantage of the material to be prepared using a simpler and sustainable synthesis methodology, as well as exhibiting a good stability at ambient conditions (temperature and humidity) over time when compared to others.

Natural kaolinitic clay: A remarkable reusable solid catalyst for the selective functional protection of aldehydes and ketones

Ponde, Datta,Borate,Sudalai,Ravindranathan,Deshpande

, p. 4605 - 4608 (1996)

Natural kaolinitic clay possessing transition metals such as Fe and Ti in its lattice has been found to catalyze efficiently the chemoselective acetalization and thioacetalization of variety of carbonyl compounds with ethane - 1,2 - diol and ethane - 1,2 - dithiol respectively.

[Hmim]3PW12O40: A high-efficient and green catalyst for the acetalization of carbonyl compounds

Dai, Yan,Li, Bin Dong,Quan, Heng Dao,Lü, Chun Xu

, p. 678 - 681 (2010)

[Hmim]3PW12O40 was developed and used in the acetalization of carbonyl compounds in excellent yields. The ionic liquid-heteropoly acid hybrid compound and reaction medium formed temperature-dependent phase-separation system with the ease of product as well as catalyst separation. The catalyst was recycled more than 10 times without any apparent loss of catalytic activity.

-

Kollonitsch,Vita

, p. 1307 (1956)

-

Direct aerobic photo-oxidative syntheses of aromatic methyl esters from methyl aromatics using anthraquinone-2,3-dicarboxylic acid as organophotocatalyst

Tada, Norihiro,Ikebata, Yuki,Nobuta, Tomoya,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika

, p. 616 - 619 (2012)

This paper reports a useful method for facile direct syntheses of aromatic methyl esters from methyl aromatics by aerobic photo-oxidation using anthraquinone-2,3-dicarboxylic acid as an organophotocatalyst.

ELECTROCHEMICAL OXIDATION OF 1-ALKENYLARENES TO GIVE BENZALDEHYDE DIMETHYL ACETALS

Ogibin, Yu. N.,Elinson, M. N.,Sokolov, A. V.,Nikishin, G. I.

, p. 432 (1990)

-

Fabrication of novel hybrid nanoflowers from boron nitride nanosheets and metal-organic frameworks: A solid acid catalyst with enhanced catalytic performance

Wang, Peng,Li, Hao,Gao, Qiang,Li, Pei-Zhou,Yao, Xin,Bai, Linyi,Nguyen, Kim Truc,Zou, Ru-Qiang,Zhao, Yanli

, p. 18731 - 18735 (2014)

A double solvent replacement method was employed for the synthesis of novel hybrid nanoflowers from boron nitride nanosheets (BNNSs) and the metal-organic framework (MOF) MIL-53 in aqueous solutions under hydrothermal treatments. The strong binding abilit

Evans

, p. 473 (1972)

Supported Iridium Catalyst for Clean Transfer Hydrogenation of Aldehydes and Ketones using Methanol as Hydrogen Source

He, Guangke,Liu, Xiang,Wang, Jing,Ye, Sen,Zhu, Jiazheng,Zhu, Longfei

, (2022/02/01)

The use of methanol as abundant and low-toxic hydrogen source under mild and clean conditions is promising for the development of safe and sustainable reduction processes, but remains a daunting challenge. This work presents a recyclable ZnO-supported Ir

Highly efficient and selectivity-controllable aerobic oxidative cleavage of C-C bond over heterogeneous Fe-based catalysts

Guo, Pengfei,Liao, Shengyun,Wang, Shun,Shi, Jing,Tong, Xinli

, p. 399 - 403 (2021/02/27)

A base-free selectivity-controllable aerobic oxidative cleavage of C-C bond with heterogeneous Fe-based catalysts (FexOy-N@C3N4) is developed. In the presence of oxygen, 1,2-diols are selectively transformed to the corresponding aldehyde, while the methyl esters are orientedly produced from 1,2-diones in methanol medium.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 1125-88-8