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933-40-4

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933-40-4 Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 61, p. 366, 1983 DOI: 10.1139/v83-065Tetrahedron Letters, 30, p. 6151, 1989 DOI: 10.1016/S0040-4039(01)93328-3

General Description

Cyclohexanone dimethyl ketal reacts with trimethylsilane in the presence of trimethylsilyl triflate to form the corresponding ether. It can also undergo allylation and propargylation in the presence of indium to form the corresponding homoallylic or homopropargylic alcohol, respectively.

Check Digit Verification of cas no

The CAS Registry Mumber 933-40-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 3 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 933-40:
(5*9)+(4*3)+(3*3)+(2*4)+(1*0)=74
74 % 10 = 4
So 933-40-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2/c1-9-8(10-2)6-4-3-5-7-8/h3-7H2,1-2H3

933-40-4 Well-known Company Product Price

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  • Aldrich

  • (458597)  Cyclohexanonedimethylketal  99%

  • 933-40-4

  • 458597-50ML

  • 1,157.13CNY

  • Detail

933-40-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclohexanone Dimethylketal

1.2 Other means of identification

Product number -
Other names 1,1-DIMETHOXYCYCLOHEXANE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:933-40-4 SDS

933-40-4Synthetic route

methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With trimethyl orthoformate at 40℃; under 6000480 Torr; for 8h;100%
With chloranil In acetonitrile for 0.5h; Irradiation;99%
With trimethyl orthoformate at 20℃; for 0.5h;98%
cyclohexanone
108-94-1

cyclohexanone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 0.33h;99%
Nafion-H In tetrachloromethane98%
With lithium tetrafluoroborate In methanol for 0.333333h; Heating;98%
Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h;89%
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h;89%
With trimethylsilyl trifluoromethanesulfonate
methanol
67-56-1

methanol

heptanal
111-71-7

heptanal

cyclohexanone
108-94-1

cyclohexanone

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

1,1-dimethoxyheptane
10032-05-0

1,1-dimethoxyheptane

Conditions
ConditionsYield
With CoCl2 for 3.5h; Heating;A n/a
B 88%
methanol
67-56-1

methanol

cyclohexyl-carbamic acid methyl ester
5817-68-5

cyclohexyl-carbamic acid methyl ester

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With tetraethylammonium tosylate electrolysis (15 F/mol, 0.5 A);69%
cyclohexanone
108-94-1

cyclohexanone

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

trimethyleneglycol
504-63-2

trimethyleneglycol

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
Stage #1: cyclohexanone; orthoformic acid triethyl ester; trimethyleneglycol With zirconium(IV) chloride In dichloromethane at 20℃; for 1h;
Stage #2: With sodium hydroxide
55%
Dimethoxymethane
109-87-5

Dimethoxymethane

1-(Trimethylsilyloxy)cyclohexene
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

2-(methoxymethyl)cyclohexanone
58173-92-5

2-(methoxymethyl)cyclohexanone

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 16℃; for 10h;A 20%
B 48%
methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

hexanedioic acid dimethyl ester
627-93-0

hexanedioic acid dimethyl ester

C

2-methoxycyclohex-2-en-1-one
23740-37-6

2-methoxycyclohex-2-en-1-one

Conditions
ConditionsYield
With cerium(IV) sulphate; oxygen at 50℃; for 8h; Oxidation; acetalization;A 38%
B 35%
C 7%
methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

1-(hydroxymethyl)cyclohexanol
15753-47-6

1-(hydroxymethyl)cyclohexanol

Conditions
ConditionsYield
With titanium(IV) dichlorodiisopropylate at 20℃; for 72h; UV-irradiation; Inert atmosphere; Overall yield = 38 %;A 29%
B 9%
methanol
67-56-1

methanol

1-iodo-1-cyclohexene
17497-53-9

1-iodo-1-cyclohexene

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

1-methoxy-cyclohex-1-ene
931-57-7

1-methoxy-cyclohex-1-ene

C

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
With zinc at 40℃; for 10h; Irradiation;A 8%
B 65 % Chromat.
C 27%
With zinc Product distribution; Further Variations:; Reagents; Irradiation; sonication;
cyclohexene
110-83-8

cyclohexene

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

3-methoxycyclohexene
2699-13-0

3-methoxycyclohexene

C

1,2-dimethoxycyclohexane
19752-95-5

1,2-dimethoxycyclohexane

Conditions
ConditionsYield
With iodosylbenzene; Dowex 50X8 acidic; FeIIIT4MPyP In methanol at 20℃; for 0.1h; Product distribution; Mechanism; other catalyst: 4-toluenesulphonic acid;A 20%
B 16%
C 14%
methanol
67-56-1

methanol

Cyclohexyl-n-butyl ether
24072-44-4

Cyclohexyl-n-butyl ether

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

1,1-dimethoxybutane
4461-87-4

1,1-dimethoxybutane

C

butanoic acid methyl ester
623-42-7

butanoic acid methyl ester

Conditions
ConditionsYield
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation;A 3.6%
B 11%
C 2.3%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With hydrogenchloride
dimethylsulfite
616-42-2

dimethylsulfite

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With hydrogenchloride; methanol
cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With methanol; tetramethylorthosilicate; phosphoric acid
methanol
67-56-1

methanol

1-iodo-1-cyclohexene
17497-53-9

1-iodo-1-cyclohexene

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
at -20℃; Irradiation;
cyclohexanone
108-94-1

cyclohexanone

N,N-dimethylformamide dimethyl sulfate adduct
89712-45-8

N,N-dimethylformamide dimethyl sulfate adduct

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
(i) MeOH, (ii) Et3N, Et2O; Multistep reaction;
methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

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

2,2-dimethoxy-propane

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;
methanol
67-56-1

methanol

cyclohexene
110-83-8

cyclohexene

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

2-methoxycyclohexane
931-56-6

2-methoxycyclohexane

C

3-methoxycyclohexene
2699-13-0

3-methoxycyclohexene

Conditions
ConditionsYield
With lithium methanolate; lithium perchlorate (electrolysis);
1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

methanol
67-56-1

methanol

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With sodium tosylate Product distribution; other ethylene ketals, electrochemical transacetalization; var. temperatures and charge;76.2 % Chromat.
With sodium tosylate at 15℃; electrolysis;76.5 % Chromat.
methanol
67-56-1

methanol

1-iodo-1-cyclohexene
17497-53-9

1-iodo-1-cyclohexene

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
at 40℃; for 10h; Irradiation;A 72 % Chromat.
B 26 % Chromat.
methanol
67-56-1

methanol

1-Methoxybicyclo-<3.1.0>-hexan
82164-76-9

1-Methoxybicyclo-<3.1.0>-hexan

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With (1,1'-biphenyl)-4,4'-dicarbonitrile Irradiation;45 % Chromat.
1-Methoxybicyclo-<3.1.0>-hexan
82164-76-9

1-Methoxybicyclo-<3.1.0>-hexan

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With (1,1'-biphenyl)-4,4'-dicarbonitrile In methanol Product distribution; Mechanism; Irradiation; other deriv. of cyclopropyl ethers; var solvents;
cyclohexanone
108-94-1

cyclohexanone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

1-azido-1-methoxycyclohexane
111238-46-1

1-azido-1-methoxycyclohexane

Conditions
ConditionsYield
With hydrogen azide; toluene-4-sulfonic acid In dichloromethane for 4h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methanol
67-56-1

methanol

1-methoxy-cyclohex-1-ene
931-57-7

1-methoxy-cyclohex-1-ene

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With lead(IV) acetate
hydrogenchloride
7647-01-0

hydrogenchloride

methanol
67-56-1

methanol

dimethylsulfite
616-42-2

dimethylsulfite

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
analoge Wirkung des Dimethylsulfits bei der Bildung von Glykosiden;
methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

1-methoxy-cyclohex-1-ene
931-57-7

1-methoxy-cyclohex-1-ene

Conditions
ConditionsYield
With 2,3,5,6-tetrachlorobenzene-1,4-diol for 0.5h; Irradiation;A 73 % Chromat.
B 26 % Chromat.
With C3H6NO9P3(6-)*4H2O*Cl(1-)*Gd(3+)*4H(1+) at 35℃; for 0.25h; Inert atmosphere;
methanol
67-56-1

methanol

cyclohexene
110-83-8

cyclohexene

A

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With carbon dioxide; oxygen; palladium dichloride at 50℃; under 105011 Torr; for 15h;A 32.4 % Chromat.
B n/a
1,1-diethoxycyclohexane
1670-47-9

1,1-diethoxycyclohexane

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / water; acetone / mesoporous aluminosilicate / 2 h / 55 °C
2: 25 percent / mesoporous aluminosilicate / 6 h / 50 °C
View Scheme
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

1-methoxycyclohexanecarbonitrile
83268-57-9

1-methoxycyclohexanecarbonitrile

Conditions
ConditionsYield
With titanium tetrachloride at -78 - -30℃;100%
With titanium tetrachloride In dichloromethane at -70 - 20℃; for 3h;92%
titanium tetrachloride In dichloromethane at -70℃; for 0.0833333h;
With titanium tetrachloride In dichloromethane at -70 - 20℃;1 g
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

2-methoxycyclohexane
931-56-6

2-methoxycyclohexane

Conditions
ConditionsYield
With trimethylsilan; trimethylsilyl trifluoromethanesulfonate In dichloromethane 0 deg C, 30 min. then 28 deg C, 14 h.;100%
With triethylsilane; Nafion-H (perfluororesinsulfonic acid) In dichloromethane for 4h; Heating;91.7 % Chromat.
Multi-step reaction with 2 steps
1: benzoyl chloride; quinoline / 60 - 70 °C
2: palladium black; diethyl ether / Hydrogenation
View Scheme
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

1-methoxy-1-(2-propenyl)-cyclohexane
60753-94-8

1-methoxy-1-(2-propenyl)-cyclohexane

Conditions
ConditionsYield
With 50 wt% silicomolybdic acid/SiO2 In acetonitrile at 20℃; for 0.16h; Hosomi-Sakurai reaction;99%
With Al-MCM-41 In dichloromethane at 30℃; for 1.5h; Sakurai allylation; Inert atmosphere;95%
With Al-MCM-41 (Si/Al = 48) In dichloromethane at 30℃; for 1.5h; Inert atmosphere;95%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

3,2'-bis-1,6:6',4'-N,O-dicarbonyl-5''-O-(triphenylmethyl)ribostamycin

3,2'-bis-1,6:6',4'-N,O-dicarbonyl-5''-O-(triphenylmethyl)ribostamycin

C60H64N4O16
72163-43-0

C60H64N4O16

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50 - 60℃; for 2h;99%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With silica gel; iron(III) chloride at 20℃; for 0.0833333h;97%
With water; Nafion-H In acetone for 0.5h;95%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

isoascorbic acid
89-65-6

isoascorbic acid

5,6-O-Cyclohexylidene-D-isoascorbic acid
97627-84-4

5,6-O-Cyclohexylidene-D-isoascorbic acid

Conditions
ConditionsYield
With tin(ll) chloride In ethyl acetate for 0.5h; Heating;99%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

3,4-O-cyclohexylidene-6-deoxy-myo-inositol
156712-80-0

3,4-O-cyclohexylidene-6-deoxy-myo-inositol

D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol
228562-73-0

D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide for 12h; Cyclization;99%
1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

2-(1-methoxy-cyclohexyl)-1-phenyl-ethanone

2-(1-methoxy-cyclohexyl)-1-phenyl-ethanone

Conditions
ConditionsYield
With MCM-41 mesoporous silica catalyst In toluene at 0℃; for 12h; Mukaiyama-aldol reaction;99%
With Al-MCM-41 In acetonitrile at 0℃; for 1h; Mukaiyama aldol reaction; Inert atmosphere;85%
With mesoporous aluminosilicate Al-MCM-41 In acetonitrile at 0℃; for 1h; Mukaiyama Aldol Addition; Inert atmosphere;85%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

4-methoxyphenyl α-L-rhamnopyranoside
18918-36-0

4-methoxyphenyl α-L-rhamnopyranoside

p-methoxyphenyl 2,3-O-cyclohexylidene-α-L-rhamnopyranoside
1028832-76-9

p-methoxyphenyl 2,3-O-cyclohexylidene-α-L-rhamnopyranoside

Conditions
ConditionsYield
camphor-10-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 3h;99%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

2-(3,4-dimethoxyphenyl)ethyl alcohol
7417-21-2

2-(3,4-dimethoxyphenyl)ethyl alcohol

6',7'-dimethoxyspiro[cyclohexane-1,1'-isochroman]
1220970-44-4

6',7'-dimethoxyspiro[cyclohexane-1,1'-isochroman]

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction;99%
With iron(II) triflate In toluene at 70℃; for 24h; Pictet-Spengler Synthesis; Green chemistry;53%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

3-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-sn-glycerol
84218-74-6

3-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-sn-glycerol

3-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-cyclohexylidene-sn-glycerol
84218-75-7

3-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-cyclohexylidene-sn-glycerol

Conditions
ConditionsYield
With toluene-4-sulfonic acid98.3%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 40℃; under 20 Torr; for 2h;98.3%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

6'-N-(benzyloxyarbonyl)-1,3,3''-tri-N-tosylkanamycin A
76550-51-1

6'-N-(benzyloxyarbonyl)-1,3,3''-tri-N-tosylkanamycin A

6'-N-(benzyloxyarbonyl)-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A
76550-52-2

6'-N-(benzyloxyarbonyl)-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A

Conditions
ConditionsYield
toluene-4-sulfonic acid In N,N-dimethyl-formamide Ambient temperature;98%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B
119783-92-5

3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B
78788-44-0, 119818-20-1

4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 2h;98%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

L-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol
156712-79-7

L-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol

L-1,2;5,6-di-O-cyclohexylidene-3-deoxy-chiro-inositol
228562-74-1

L-1,2;5,6-di-O-cyclohexylidene-3-deoxy-chiro-inositol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide for 12h; Cyclization;98%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

2-(1-hydroxy-cyclohexylmethyl)-acrylic acid methyl ester

2-(1-hydroxy-cyclohexylmethyl)-acrylic acid methyl ester

Conditions
ConditionsYield
With indium In tetrahydrofuran; water at 20℃; for 6h;98%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

1,3,2',7',4
82002-36-6

1,3,2',7',4"-pentakis-N-(benzyloxycarbonyl)apramycin

1,3,2',7',4

1,3,2',7',4"-pentakis-N-(benzyloxycarbonyl)-5,6:2",3"-di-O-cyclohexylideneapramycin

Conditions
ConditionsYield
Stage #1: cycloxexanone dimethyl ketal; 1,3,2',7',4"-pentakis-N-(benzyloxycarbonyl)apramycin With toluene-4-sulfonic acid; triethylamine In N,N-dimethyl-formamide at 60℃; for 4h;
Stage #2: With acetic acid In 1,4-dioxane; water at 20℃; for 18h;
98%
methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside
34299-66-6

methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

methyl 4,6-O-cyclohexylidene-2-deoxy-2-(methoxycarbonyl)amino-α-D-glucopyranoside
69477-57-2

methyl 4,6-O-cyclohexylidene-2-deoxy-2-(methoxycarbonyl)amino-α-D-glucopyranoside

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 15 Torr; for 1.5h;97%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

D-gulono-1,4-lactone
6322-07-2

D-gulono-1,4-lactone

2,3:5,6-O-dicyclohexylidene D-gulono-lactone
119680-72-7

2,3:5,6-O-dicyclohexylidene D-gulono-lactone

Conditions
ConditionsYield
With 4 A molecular sieve; toluene-4-sulfonic acid In benzene for 10h; Heating;97%
With toluene-4-sulfonic acid In benzene for 10h; Heating;
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

4'',6''-O-Benzylidene-6'-N,4'-O-carbonyl-1,3,3''-tri-N-tosylkanamycin A

4'',6''-O-Benzylidene-6'-N,4'-O-carbonyl-1,3,3''-tri-N-tosylkanamycin A

4'',6''-O-Benzylidene-6'-N,4'-O-carbonyl-2',3'-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A
93070-01-0

4'',6''-O-Benzylidene-6'-N,4'-O-carbonyl-2',3'-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A

Conditions
ConditionsYield
With 5A molecular sieve; trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide for 6h; Heating;97%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

(2R,3R,4S)-5-Iodo-2,4-dimethyl-hex-5-ene-1,3-diol
204448-53-3

(2R,3R,4S)-5-Iodo-2,4-dimethyl-hex-5-ene-1,3-diol

(2R,3R)-2-((S)-2-Iodo-1-methyl-allyl)-3-methyl-1,5-dioxa-spiro[5.5]undecane
204448-28-2

(2R,3R)-2-((S)-2-Iodo-1-methyl-allyl)-3-methyl-1,5-dioxa-spiro[5.5]undecane

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate97%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

mannitol
69-65-8

mannitol

(1R,2R)-1,2-di-[(S)-1,4-dioxaspiro[4.5]dec-2-yl]-ethane-1,2-diol

(1R,2R)-1,2-di-[(S)-1,4-dioxaspiro[4.5]dec-2-yl]-ethane-1,2-diol

Conditions
ConditionsYield
Stage #1: mannitol With toluene-4-sulfonic acid In N,N-dimethyl-formamide Heating;
Stage #2: cycloxexanone dimethyl ketal at 60℃; for 1h; Heating;
96%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

(3R,5S)-tert-butyl 3,5-dihydroxyhexanoate
126080-51-1, 139209-91-9, 139209-89-5

(3R,5S)-tert-butyl 3,5-dihydroxyhexanoate

C16H28O4

C16H28O4

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 18h;96%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

1-methoxy-cyclohex-1-ene
931-57-7

1-methoxy-cyclohex-1-ene

Conditions
ConditionsYield
Heating;95%
With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature;94%
With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature;94%
3-cyano-2H-cycloheptafuran-2-one
53617-66-6

3-cyano-2H-cycloheptafuran-2-one

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

1-Cyano-2,3-tetramethylenazulen
33658-65-0

1-Cyano-2,3-tetramethylenazulen

Conditions
ConditionsYield
at 160 - 190℃;95%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine
22854-75-7

N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine

1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine
55728-75-1

1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine

Conditions
ConditionsYield
Stage #1: cycloxexanone dimethyl ketal; N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere;
Stage #2: In methanol; N,N-dimethyl-formamide at 50℃; for 1h;
Stage #3: With triethylamine In methanol; N,N-dimethyl-formamide at 20℃;
95%
With 5A molecular sieve; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid 1.) DMF, CH2Cl2, 6 h, reflux; 2.) ethanol, 25 deg C, 16 h; Yield given. Multistep reaction;
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin C
133036-39-2

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin C

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C
133036-40-5

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 16h; Ambient temperature;95%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

(3R,4S,5R)-3,4,5-trihydroxycyclohexanone ethylene dithioacetal
77003-65-7

(3R,4S,5R)-3,4,5-trihydroxycyclohexanone ethylene dithioacetal

(3R,4S,5R)-4,5-O-cyclohexylidene-4,5-dioxy-3-hydroxycyclohexanone ethylene dithioacetal

(3R,4S,5R)-4,5-O-cyclohexylidene-4,5-dioxy-3-hydroxycyclohexanone ethylene dithioacetal

Conditions
ConditionsYield
With sulfuric acid In N,N-dimethyl-formamide for 24h; Ambient temperature;95%
With sulfuric acid In N,N-dimethyl-formamide85%
With sulfuric acid In N,N-dimethyl-formamide for 6h;85%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

5,5-(ethylenedithio)-1,2,3-cyclohexanetriol

5,5-(ethylenedithio)-1,2,3-cyclohexanetriol

2,3-(1,1-cyclohexylenedioxy)-5,5-(ethylenedithio)cyclohexanol

2,3-(1,1-cyclohexylenedioxy)-5,5-(ethylenedithio)cyclohexanol

Conditions
ConditionsYield
With sulfuric acid In N,N-dimethyl-formamide95%

933-40-4Relevant articles and documents

In-situ crystallization route to nanorod-aggregated functional ZSM-5 microspheres

Li, Bin,Sun, Bo,Qian, Xufang,Li, Wei,Wu, Zhangxiong,Sun, Zhenkun,Qiao, Minghua,Duke, Mikel,Zhao, Dongyuan

, p. 1181 - 1184 (2013)

Herein, we develop a reproducible in situ crystallization route to synthesize uniform functional ZSM-5 microspheres composed of aggregated ZSM-5 nanorods and well-dispersed uniform Fe3O4 nanoparticles (NPs). The growth of such unique microspheres undergoes a NP-assisted recrystallization process from surface to core. The obtained magnetic ZSM-5 microspheres possess a uniform size (6-9 μm), ultrafine uniform Fe 3O4 NPs (~10 nm), good structural stability, high surface area (340 m2/g), and large magnetization (~8.6 emu/g) and exhibit a potential application in Fischer-Tropsch synthesis.

Facile synthesis of hollow zeolite microspheres through dissolution-recrystallization procedure in the presence of organosilanes

Tao, Haixiang,Ren, Jiawen,Liu, Xiaohui,Wang, Yanqin,Lu, Guanzhong

, p. 179 - 188 (2013)

Hollow zeolite microspheres have been hydrothermally synthesized in the presence of organosilanes via a dissolution-recrystallization procedure. In the presence of organosilanes, zeolite particles with a core/shell structure formed at the first stage of hydrothermal treatment, then the core was consumed and recrystallized into zeolite framework to form the hollow structure during the second hydrothermal process. The influence of organosilanes was discussed, and a related dissolution-recrystallization mechanism was proposed. In addition, the hollow zeolite microspheres exhibited an obvious advantage in catalytic reactions compared to conventional ZSM-5 catalysts, such as in the alkylation of toluene with benzyl chloride. Copyright

CoFe2O4 Nanocrystals Mediated Crystallization Strategy for Magnetic Functioned ZSM-5 Catalysts

Li, Bin,Yildirim, Erol,Li, Wei,Qi, Dianpeng,Yu, Jiancan,Wei, Jiaqi,Liu, Zhiyuan,Sun, Zhenkun,Liu, Yong,Kong, Biao,Xue, Zhaoteng,Liu, Zhuangjian,Yang, Shuo-Wang,Chen, Xiaodong,Zhao, Dongyuan

, (2018)

Zeolites have many applications in the petrochemical and fine chemical industry and their functionalization does expand the spectrum of potentials. However, the integration of functional nanocrystals into zeolite frameworks with controlled size, dispersion, and crystallization behavior still remains a significant challenge. Here, a new synthesis of magnetic functioned ZSM-5 zeolite catalysts via a CoFe2O4 nanocrystal mediated crystallization strategy is reported. It is found that high crystallinity of CoFe2O4 nanocrystals results in a well-dispersed encapsulation of them into a single-crystal of ZSM-5 due to non-further-grown nanocrystals during the fast ZSM-5 growth. On the contrary, low crystallinity of CoFe2O4 nanocrystals leads to the polycrystalline zeolite growth due to the secondary growth of nanocrystals accompanied by the zeolite crystallization and large lattice mismatch between them. The successful encapsulation of small CoFe2O4 nanocrystals (≈4 nm) into single crystals lies on the preattachment of them into solid silica gel. During the growth of ZSM-5 crystals, no secondary growth of nanocrystals happens and its motion is restricted. The encapsulation of magnetic CoFe2O4 nanocrystals not only endows magnetic function into zeolites for the first time, but also does not impact catalytic performance of ZSM-5 in acetalization of cyclohexanone with methanol, which is highly promising in catalytic industries.

Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I

Cao, Fu-Rong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing

, (2021/06/21)

A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild reaction condition, short reaction time, recyclable of catalyst and broad substrates scope with excellent yields.

Facile synthesis of acetal over a supported novel Br?nsted and lewis acid ionic liquid catalyst

Liu, Ruifeng,Dai, Liming,Zhao, Qian,Xie, Yingjie,Jiang, Tingshun

, p. 4396 - 4405 (2019/05/08)

A novel Br?nsted and Lewis acid ionic liquid (IL) chlorinated butyrolactam chlorozincinate (CPCl-ZnCl2) was synthesized by a hydrothermal process and characterized by Fourier transform infrared (FT-IR). The Fe-SBA-15 mesoporous materials with different Si/Fe mole ratios were prepared by direct synthesis method. The supported ionic liquid (IL/Fe-SBA-15) with various IL contents were prepared by a wet impregnation method and characterized by X-ray diffraction (XRD), Transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and N2 physical adsorption. The acidity was measured by FT-IR spectroscopy using pyridine as probes. The catalytic property was tested in acetalization of cyclohexanone with ethylene glycol. The results demonstrated that the IL/Fe-SBA-15 catalysts were of higher catalytic activity compared to Fe-SBA-15. Under optimal conditions, the acetalization could reach to 92.6% cyclohexanone conversion with 99.3% acetal selectivity. After 5 cycles, the cyclohexanone conversion decreased slightly. Also, the catalyst showed good catalytic property in the other acetalization of cyclohexanone and benzyl alcohol.

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