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100-06-1

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100-06-1 Usage

Identification

▼▲ CAS.No.:? 100-06-1? FL.No.:? 7.038 FEMA.No.:? 2005 NAS.No.:? 2005 CoE.No.:? 570 EINECS.No.:? 202-815-9? JECFA.No.:? 810

Description

Yellowish-white crystals with an odor similar to that of p-methylacetopheneone, suggestive of hawthorn and floral note of heliotrope, possessing a bitter and unpleasant taste. Useful in vanilla, nut, tobacco and butter flavors.

Regulatory Status

CoE: Approved. Bev.: 10 ppm; Food: 20 ppm FDA: 21 CFR 172.515 FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2001).

Usage

Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Alcoholic.beverages? 0.0001 0.0001 Baked.goods? 1.5 2 Chewing.gum? 110 110 Frozen.dairy? 1 2 Gelatins,.puddings? 0.2 0.2 Hard.candy? 278.3 335 Meat.products? 100 100 Nonalcoholic.beverages? 7.8 150 Soft.candy? 2.1 31

Natural occurrence

Reported found in European cranberry (Vaccinium oxycoccus L.), guava fruit (Psidium guajava L.), Vitis labrusca L., tomato, anise (Pimpinella anisum L.), mentha oils, grilled and roasted beef, sherry, cloudberry (Rubus chamaemorus L.), salted and pickled plums, Illicium verum and black chokeberry (Aronia melanocarpa ell.).

Chemical Properties

Different sources of media describe the Chemical Properties of 100-06-1 differently. You can refer to the following data:
1. WHITE CRYSTALS OR CRYSTALLINE POWDER
2. 4-Methoxyacetophenone occurs in anise oil. It forms white crystals (mp 38°C) with a sweet odor, reminiscent of hawthorn. 4-Methoxyacetophenone is prepared by Friedel–Crafts acetylation of anisole. A modern process uses ??-zeolites as Friedel–Crafts catalysts in combination with a continuous flow technology. 4-Methoxyacetophenone is used in soap perfumes
3. Yellowish-white crystals with an odor similar to that of p-methylacetopheneone, suggestive of hawthorn and floral note of heliotrope, possessing a bitter and unpleasant taste. Useful in vanilla, nut, tobacco and butter flavors

Occurrence

Reported found in European cranberry (Vaccinium oxycoccus L.), guava fruit (Psidium guajava L.), Vitis labrusca L., tomato, anise (Pimpinella anisum L.), mentha oils, grilled and roasted beef, sherry, cloudberry (Rubus chamaemorus L.), salted and pickled plums, Illicium verum and black chokeberry (Aronia melanocarpa ell.).

Uses

Different sources of media describe the Uses of 100-06-1 differently. You can refer to the following data:
1. 4'-Methoxyacetophenone is used as a component of perfumes and as chemical intermediate in the manufacture of pharmaceuticals, resins, flavouring agents. And also used to study ruthenium catalyzed step growth copolymerization of 4?-methoxyacetophenone with α,ω-dienes to yield copolymers.
2. 4'-Methoxyacetophenone is a solid, pale yellow flavoring agent with a hawthornlike odor. It is soluble in most fixed oils and propylene glycol, and it is insoluble in glycerin and mineral oil. It is obtained by chemical synthesis. This flavoring substance or its adjuvant may be safely used in food in the minimum quantity required to produce its intended flavor. It can be used alone or in combination with other flavoring substances or adjuvants. It is also termed p-methoxyacetophenone.
3. Perfumery (for floral odors), flavoring.

Definition

ChEBI: A member of the class of acetophenones that is acetophenone substituted by a methoxy group at position 4.

Preparation

From anisole and acetyl chloride in the presence of aluminum chloride and carbon disulfide; from anisole and acetic acid in the presence of boron trifluoride.

Taste threshold values

Taste characteristics at 10 ppm: sweet, anisic, fruity, cherry with powdery vanilla nuances.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 5414, 1981 DOI: 10.1021/jo00339a036Synthetic Communications, 26, p. 291, 1996 DOI: 10.1080/00397919608003617Tetrahedron Letters, 35, p. 9471, 1994 DOI: 10.1016/S0040-4039(00)78574-1

General Description

4′-Methoxyacetophenone undergoes biocatalytic enantioselective reduction using immobilized Rhodotorula sp. AS2.2241 cells to yield (S)-1-(4-methoxyphenyl) ethanol in a hydrophilic ionic liquid-containing co-solvent system.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion. Human systemic effects by inhalation: pulse rate increase without fall in blood pressure and blood pressure elevation. A skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Purification Methods

Crystallise the ketone from diethyl ether/pet ether. [Beilstein 8 IV 340.]

Check Digit Verification of cas no

The CAS Registry Mumber 100-06-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 100-06:
(5*1)+(4*0)+(3*0)+(2*0)+(1*6)=11
11 % 10 = 1
So 100-06-1 is a valid CAS Registry Number.

100-06-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11162)  4'-Methoxyacetophenone, 99%   

  • 100-06-1

  • 25g

  • 153.0CNY

  • Detail
  • Alfa Aesar

  • (A11162)  4'-Methoxyacetophenone, 99%   

  • 100-06-1

  • 250g

  • 321.0CNY

  • Detail
  • Alfa Aesar

  • (A11162)  4'-Methoxyacetophenone, 99%   

  • 100-06-1

  • 1000g

  • 815.0CNY

  • Detail
  • Sigma-Aldrich

  • (52222)  4′-Methoxyacetophenone  analytical standard

  • 100-06-1

  • 52222-100MG

  • 615.42CNY

  • Detail

100-06-1SDS

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 4-methoxyacetophenone

1.2 Other means of identification

Product number -
Other names Ethanone, 1-(4-methoxyphenyl)-

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:100-06-1 SDS

100-06-1Synthetic route

4-Methoxystyrene
637-69-4

4-Methoxystyrene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 4h; Wacker Oxidation;100%
With water; oxygen In methanol; dimethyl sulfoxide at 80℃; under 1520.1 Torr; for 20h; Wacker Oxidation; Autoclave;99%
With palladium diacetate; 9-tert-butyl-10-methylanthracene ozonide In acetonitrile for 72h; Ambient temperature;93%
rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; oxygen; sodium hydrogencarbonate; gold(I) chloride In water at 100℃; under 38002.6 Torr; for 24h;100%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In pentane for 5h; Reflux;100%
With diisopropoxyaluminium trifluoroacetate; 4-nitrobenzaldehdye In benzene for 0.25h; Ambient temperature;99%
acetic anhydride
108-24-7

acetic anhydride

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With polystyrene-bound tetrafluorophenylbis(triflyl)methane In nitromethane at 50℃; for 2h; Friedel-Crafts acylation;100%
With lithium perchlorate at 60℃; for 1h;100%
With Sulfate; zirconium(IV) oxide at 110℃;100%
acetic acid
64-19-7

acetic acid

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: acetic acid; methoxybenzene With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h;
Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h;
100%
With methanesulfonic acid; pyrographite at 80℃; for 0.333333h; Friedel-Crafts acylation;98%
With aluminum oxide; trifluoroacetic anhydride for 0.166667h; Ambient temperature;96%
1-(1,1-Bis-ethylsulfanyl-ethyl)-4-methoxy-benzene
128881-90-3

1-(1,1-Bis-ethylsulfanyl-ethyl)-4-methoxy-benzene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With gallium(III) trichloride In dichloromethane; water for 0.25h; Ambient temperature;100%
methoxybenzene
100-66-3

methoxybenzene

N,N-diacetyl-p-nitrophenylsulphenamide
79562-11-1

N,N-diacetyl-p-nitrophenylsulphenamide

A

4-(4-methoxyphenylsulfanyl)nitrobenzene
22865-50-5

4-(4-methoxyphenylsulfanyl)nitrobenzene

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With trifluoroacetic acid at 190 - 200℃;A 100%
B 21%
4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With gold(III) tribromide; water at 200℃; for 0.333333h; microwave irradiation;100%
With Au nanoparticles covalently bonded to HS/SO3H functionalized periodic mesoporous organosilica (Et) at 70℃; for 1.5h; neat (no solvent);100%
With hydrogenchloride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 48℃; for 20h; Solvent; Schlenk technique; Inert atmosphere;100%
2-Bromo-4'-methoxyacetophenone
2632-13-5

2-Bromo-4'-methoxyacetophenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With AcrH2 In acetonitrile at 298℃; for 19h; Irradiation;100%
With AcrH2 In acetonitrile at 298℃; for 19h; Irradiation;100%
With decaborane; palladium on activated charcoal In methanol at 20℃; for 2h;99%
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

methyl iodide
74-88-4

methyl iodide

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;100%
With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 25℃; for 2h; Williamson synthesis;99%
With potassium carbonate In acetone Heating;98%
4-methoxyacetophenone semicarbazone
717-14-6

4-methoxyacetophenone semicarbazone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With hydrogenchloride; Tonsil In ethyl acetate for 1.5h; Heating;100%
With CuCl2*2H2O for 0.00277778h; microwave irradiation;95%
With benzyltriphenylphosphonium dichromate; silica gel for 0.25h;95%
methoxybenzene
100-66-3

methoxybenzene

acetyl chloride
75-36-5

acetyl chloride

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at -10℃; for 0.25h;99%
With zinc at 80 - 82℃; for 0.00194444h; Friedel-Crafts acylation; microwave irradiation;99%
With indium(III) tosylate In dodecane; nitromethane for 1h; Friedel-Crafts Acylation; Schlenk technique; Reflux;99%
4-methoxyacetophenone oxime
2475-92-5

4-methoxyacetophenone oxime

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 4-methoxyacetophenone oxime With hexachlorodisilane; silica gel In toluene at 110℃; for 0.5h;
Stage #2: With water In toluene for 0.5h;
99%
With N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide) In tetrachloromethane at 20℃; for 2h; Product distribution;97%
With formaldehyd; sodium dodecyl-sulfate In water at 50℃; for 2h; Ultrasound irradiation;97%
p-ethylanisole
1515-95-3

p-ethylanisole

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With oxygen In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 6h; Irradiation;99%
With tert.-butylhydroperoxide In chlorobenzene at 99.84℃; for 10h;98%
With dihydroxy-methyl-borane; bathophenanthroline; copper (I) acetate; lithium carbonate; N-fluorobis(benzenesulfon)imide In chlorobenzene at 45℃; for 16h;96%
2-(4-methoxyphenyl)-2-methyI-1,3-dioxolane
36881-00-2

2-(4-methoxyphenyl)-2-methyI-1,3-dioxolane

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With cerium triflate In nitromethane; water at 20℃; for 6h;99%
With water at 120℃; for 0.5h; microwave irradiation;99%
With Montmorillonite K 10; water In acetone for 0.5h; Heating;97%
1-(4-methoxy-phenyl)-2-phenoxy-ethanone
19513-78-1

1-(4-methoxy-phenyl)-2-phenoxy-ethanone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With ammonium chloride; zinc In ethanol for 0.5h; Heating;99%
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 3h; Schlenk technique; Inert atmosphere;92%
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 20 °C
2: sodium salt of dibutyl phosphate; Methyl thioglycolate; [Ir(ppy)2(dtbpy)]PF6 / N,N-dimethyl acetamide / 24 h / 25 °C / Irradiation; Sealed tube; Inert atmosphere
View Scheme
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere;A 99%
B 99%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction;A 95%
B 72%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; Reagent/catalyst; Irradiation; chemoselective reaction;A 89%
B 88%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 1h;A 95%
B 99%
With 5%-palladium/activated carbon; ammonium formate In water at 80℃; for 1h;A n/a
B 98%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 89%
B 86%
2',3',4',5',6'-pentamethylacetophenone
2040-01-9

2',3',4',5',6'-pentamethylacetophenone

methoxybenzene
100-66-3

methoxybenzene

A

2-Methoxyacetophenone
579-74-8

2-Methoxyacetophenone

B

pentamethylbenzene,
700-12-9

pentamethylbenzene,

C

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
trifluoroacetic acid for 20h; Heating;A n/a
B 98%
C n/a
With sodium 2,2,2-trifluoroacetate; trifluoroacetic acid for 0.5h; Product distribution; Rate constant; Heating; with various additives and additive amounts;A n/a
B 38%
C n/a
4-methoxyacetophenone phenylhydrazone
24310-46-1

4-methoxyacetophenone phenylhydrazone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With benzyltriphenylphosphonium dichromate; silica gel for 0.116667h;98%
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate In acetonitrile for 0.75h; Oxidation; Heating;97%
With Oxone; water; potassium hydrogencarbonate In acetone for 0.5h; Heating;97%
p-Methoxyacetophenone N,N-dimethylhydrazone
5757-98-2

p-Methoxyacetophenone N,N-dimethylhydrazone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 0.916667h; Heating;98%
With Oxone; water; potassium hydrogencarbonate In acetonitrile for 0.5h; Heating;98%
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.583333h; Oxidation; Heating;98%
acetic anhydride
108-24-7

acetic anhydride

methoxybenzene
100-66-3

methoxybenzene

A

acetic acid
64-19-7

acetic acid

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With lanthanum(lll) triflate In nitromethane at 50℃; for 24h; Kinetics; Product distribution; Further Variations:; Temperatures; Solvents; Reagents; Friedel-Crafts acylation;A n/a
B 98%
Ce-Clay at 100℃; for 1 - 5h;A n/a
B 35%
La-Clay at 100℃; for 1 - 5h;A n/a
B 15%
1-(4-methoxyphenyl)-2-phenoxyethan-1-ol
29509-29-3

1-(4-methoxyphenyl)-2-phenoxyethan-1-ol

A

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 135℃; for 4h; Inert atmosphere;A 98%
B n/a
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 1h;A 98%
B n/a
With [Ir(ppy)2(dtbpy)]PF6; sodium salt of dibutyl phosphate; Methyl thioglycolate In N,N-dimethyl acetamide at 25℃; for 24h; Reagent/catalyst; Solvent; Irradiation; Sealed tube; Inert atmosphere;A 86%
B 71%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 5%-palladium/activated carbon; ammonium formate In ethanol; water at 80℃; for 1h;98%
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 3h; Schlenk technique; Inert atmosphere;89%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 12h; Irradiation; chemoselective reaction;
1-(4-methoxyphenyl)-2-phenoxyethan-1-ol
29509-29-3

1-(4-methoxyphenyl)-2-phenoxyethan-1-ol

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 5%-palladium/activated carbon; ammonium formate In tert-butyl methyl ether; water at 80℃; for 3h;98%
1-(4-methoxyphenyl)-2-(naphthalen-2-yloxy)ethan-1-one
296278-03-0

1-(4-methoxyphenyl)-2-(naphthalen-2-yloxy)ethan-1-one

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 3h; Schlenk technique; Inert atmosphere;98%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

A

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; phenylsilane; iron(II) chloride In ethanol at 20℃; for 4.5h; Reagent/catalyst; Wacker Oxidation;A 2%
B 97%
With triethylsilane; (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyaninato)iron(II); oxygen In ethanol at 20℃; under 760.051 Torr; for 9.5h; Wacker Oxidation; Sealed tube; Green chemistry; chemoselective reaction;A 12%
B 85%
With sodium hydroxide; sodium tetrahydroborate; oxygen; 5,10,15,20-tetrakis(1-methyl-4-pyridino)porphyrine tertachloride In water Ambient temperature; pH 12;A 14%
B 65%
With triethylsilane; [5,10,15,20-tetra(2,6-dichlorophenyl)porphyrinato]cobalt(II); oxygen; phosphorous acid trimethyl ester 1.) 2-propanol, dichloromethane, 28 deg C, 1 atm, 30 min, 2.) 2-propanol, dichloromethane, RT, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

p-methoxybenzoylmethanol
4136-21-4

p-methoxybenzoylmethanol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
In acetone at 25℃; for 3h;A 3%
B 97%
In acetone at 25℃; for 3h; Thermodynamic data; Rate constant; Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.);A 3%
B 97%
sodium bicarbonate NaHCO3

sodium bicarbonate NaHCO3

triethylaluminum (C2H5)3Al

triethylaluminum (C2H5)3Al

methoxybenzene
100-66-3

methoxybenzene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With potassium chloride; acetic anhydride In nitromethane; toluene97%
1-(4-methoxyphenyl)ethanamine
6298-96-0

1-(4-methoxyphenyl)ethanamine

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With 4-phenylnaphthalene-1,2-dione In acetonitrile at 80℃; for 36h;97%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; pH=4.5; Enzymatic reaction;84%
With caesium carbonate; dibenzoyl peroxide In N,N-dimethyl-formamide at 0 - 50℃;69%
benzaldehyde
100-52-7

benzaldehyde

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

trans-4'-methoxychalcone
22966-19-4

trans-4'-methoxychalcone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.025h; Irradiation;100%
With 4 A molecular sieve; NAP-MgO In toluene for 16h; Claisen-Schmidt condensation; Heating;98%
With sodium hydroxide In ethanol at 20℃; Cooling with ice;95%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(E)-1,3-bis(4-methoxyphenyl)-2-propene-1-one
41564-67-4

(E)-1,3-bis(4-methoxyphenyl)-2-propene-1-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 20h; Aldol Condensation;100%
With sodium hydroxide In ethanol at 20℃; for 48h;99%
With sodium hydroxide In ethanol at 20℃; for 48h; Claisen-Schmidt Condensation;98%
oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

ethyl 3-(4-methoxybenzoyl)pyruvate
35322-20-4

ethyl 3-(4-methoxybenzoyl)pyruvate

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)ethanone With sodium In ethanol at 20℃; for 0.5h;
Stage #2: oxalic acid diethyl ester at 20 - 80℃; for 3h;
100%
With sodium hydride In N,N-dimethyl-formamide at 0 - 100℃;100%
Stage #1: oxalic acid diethyl ester With sodium methylate In diethyl ether at 20℃; Inert atmosphere;
Stage #2: 1-(4-methoxyphenyl)ethanone In diethyl ether at 20℃; for 12h;
92%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere;100%
Stage #1: 1-(4-methoxyphenyl)ethanone With C24H20Cl2F5NRuS; isopropyl alcohol at 82℃; for 0.166667h;
Stage #2: With potassium hydroxide at 82℃; for 1h;
100%
With hydrogen; Ru(1,3-dimesityl-2,3-dihydro-1H-imidazol-2-yl)(PPh3)2CO(H)2 In benzene at 70℃; under 3800 Torr; for 24h;99%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

4-methoxyacetophenone oxime
2475-92-5

4-methoxyacetophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;100%
With pyridine; hydroxylamine hydrochloride In ethanol at 75℃; for 22h;99%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

p-methoxyphenylglyoxal
1076-95-5

p-methoxyphenylglyoxal

Conditions
ConditionsYield
With selenium (IV) oxide In 1,4-dioxane; water Heating;100%
With tris(2,2'-bipyridyl)ruthenium dichloride; dioxane dibromide; sodium L-ascorbate In acetonitrile at 20℃; for 8h; Irradiation; Green chemistry;91%
With selenium(IV) oxide In 1,4-dioxane for 3h; Reflux;88%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

2-Bromo-4'-methoxyacetophenone
2632-13-5

2-Bromo-4'-methoxyacetophenone

Conditions
ConditionsYield
With bromine In 1,4-dioxane; diethyl ether for 0.5h; Ambient temperature;100%
With N-Bromosuccinimide; toluene-4-sulfonic acid In chloroform at 20℃; for 12h;98.7%
With bis(dimethylacetamide)hydrogen tribromide In methanol at 20 - 45℃; for 0.25h;96%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

p-ethylanisole
1515-95-3

p-ethylanisole

Conditions
ConditionsYield
With hydrogen under 2250.23 Torr; for 4h;100%
With palladium dichloride In methanol at 40℃; for 24h; Inert atmosphere; Green chemistry; chemoselective reaction;99%
With hydrogen In 1,4-dioxane at 200℃; under 15001.5 Torr;98.9%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

1,5-diethoxy-1,5-di(p-methoxyphenyl)penta-2,4-dienylium perchlorate

1,5-diethoxy-1,5-di(p-methoxyphenyl)penta-2,4-dienylium perchlorate

Conditions
ConditionsYield
With perchloric acid for 0.666667h;100%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

methyl 3-(4-methoxybenzoyl)acetate
22027-50-5

methyl 3-(4-methoxybenzoyl)acetate

Conditions
ConditionsYield
With sodium hydride In toluene at 110℃;100%
Stage #1: carbonic acid dimethyl ester With sodium hydride In toluene at 110℃;
Stage #2: 1-(4-methoxyphenyl)ethanone In toluene at 110℃;
100%
With sodium hydride In toluene for 4h; Inert atmosphere; Reflux;98%
1-(4-methoxyphenyl)-3,3-bis(methylsulfanyl)propenone
33868-76-7

1-(4-methoxyphenyl)-3,3-bis(methylsulfanyl)propenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(E)-1,5-Bis-(4-methoxy-phenyl)-3-methylsulfanyl-pent-2-ene-1,5-dione
78227-65-3

(E)-1,5-Bis-(4-methoxy-phenyl)-3-methylsulfanyl-pent-2-ene-1,5-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 3h; Ambient temperature;100%
1-(4-methoxyphenyl)-3,3-bis(methylsulfanyl)propenone
33868-76-7

1-(4-methoxyphenyl)-3,3-bis(methylsulfanyl)propenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(E)-1,5-Bis-(4-methoxy-phenyl)-3-methylsulfanyl-pent-2-ene-1,5-dione
78227-65-3

(E)-1,5-Bis-(4-methoxy-phenyl)-3-methylsulfanyl-pent-2-ene-1,5-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran Ambient temperature;100%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

4-(4-methoxy-phenyl)-[1,2,3]thiadiazole
18212-22-1

4-(4-methoxy-phenyl)-[1,2,3]thiadiazole

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)ethanone With polystyrene-sulfonylhydrazide resin; acetic acid In tetrahydrofuran at 50℃; for 4h; Solid phase reaction;
Stage #2: With thionyl chloride In 1,2-dichloro-ethane at 60℃; for 5h; Solid phase reaction; Hurd-Mori cyclization;
100%
With iodine; potassium thioacyanate; toluene-4-sulfonic acid hydrazide; copper dichloride In dimethyl sulfoxide at 100℃; for 1h; Sealed tube;81%
With iodine; potassium thioacyanate; toluene-4-sulfonic acid hydrazide; copper(l) chloride In dimethyl sulfoxide at 130℃; for 1h;81%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

4-methoxyphenyl acetate
1200-06-2

4-methoxyphenyl acetate

Conditions
ConditionsYield
With Mg10Al2(OH)24CO3; oxygen; benzaldehyde In 1,2-dichloro-ethane at 40℃; for 24h;100%
With bis-trimethylsilanyl peroxide; 4 A molecular sieve; tin(IV) chloride; rac-diaminocyclohexane In tetrahydrofuran; dichloromethane for 3h; Ambient temperature;97%
With 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) In dichloromethane for 1h; Ambient temperature;95%
(S(S)R)-(+)-3-methyl-2-pivaloyl-2,3-dihydroisothiazole 1-oxide
139343-81-0

(S(S)R)-(+)-3-methyl-2-pivaloyl-2,3-dihydroisothiazole 1-oxide

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

N-((R)-1-{2-[(S)-2-(4-Methoxy-phenyl)-2-oxo-ethanesulfinyl]-phenyl}-ethyl)-2,2-dimethyl-propionamide
174736-11-9

N-((R)-1-{2-[(S)-2-(4-Methoxy-phenyl)-2-oxo-ethanesulfinyl]-phenyl}-ethyl)-2,2-dimethyl-propionamide

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran; toluene 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; -78 deg C to r.t.;100%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(S)-1-(4-Methoxyphenyl)ethanol
1517-70-0, 1572-97-0, 3319-15-1, 43230-31-5

(S)-1-(4-Methoxyphenyl)ethanol

Conditions
ConditionsYield
With dimethylsulfide borane complex; 4-chloro-2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylamino)methyl)phenol In tetrahydrofuran for 2h; Inert atmosphere; Reflux; optical yield given as %ee; enantioselective reaction;100%
diethylzinc; (+)-N,N'-Bis<(R)-1-phenylethyl>-1,2-ethylendiamin99%
With (mer-[(S,S)-1,5-dimethyl-2,4-bis(4-phenyl-1,3-oxazolin-2-yl)benzene(1-)]Ru(CO)Cl)2(ZnCl2); hydrogen; sodium methylate; (-)-(S)-1-Anthracen-9-ylethanol In isopropyl alcohol at 40℃; under 22801.5 Torr; for 24h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction;99%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(R)-1-(4-Methoxyphenyl)ethanol
1517-70-0

(R)-1-(4-Methoxyphenyl)ethanol

Conditions
ConditionsYield
With (S,S)-RuCl2(2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)(1,1-dianisyl-2-isopropyl-1,2-ethylenediamine); potassium tert-butylate; hydrogen In isopropyl alcohol at 26 - 30℃; under 7600 Torr; for 1h;100%
With Trimethyl borate; (S)-diphenylprolinol; dimethylsulfide borane complex In tetrahydrofuran; toluene at 25℃;99%
With potassium tert-butylate; hydrogen; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (R)-Ph-BINAN-H-Py In isopropyl alcohol at 25℃; under 38000 Torr; for 15h;99.3%
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(E)-1-(4-methoxyphenyl)ethanone oxime
2475-92-5

(E)-1-(4-methoxyphenyl)ethanone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;100%
With hydroxylamine hydrochloride; sodium acetate In methanol Reflux;100%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one
18096-70-3

3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3.5h; Reflux;100%
In N,N-dimethyl-formamide for 24h; Reflux;98%
In neat (no solvent) at 160℃; for 0.25h; Microwave irradiation;95%
formaldehyd
50-00-0

formaldehyd

4-benzylpyperidine
31252-42-3

4-benzylpyperidine

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

C35H44N2O2
1037020-22-6

C35H44N2O2

Conditions
ConditionsYield
With hydrogenchloride In ethanol Mannich reaction; Heating;100%

100-06-1Relevant articles and documents

Regeneration of carbonyl compounds by oxidative cleavage of oximes with NBS in the presence of β-cyclodextrin in water

Reddy, M. Somi,Narender,Rao, K. Rama

, p. 3875 - 3881 (2004)

The conversion of different oximes to the corresponding carbonyl compounds was carried out at room temperature in good to high yields with N-bromosuccinimide in water in the presence of β-cyclodextrin.

First example of water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols

Ajjou, Abdelaziz Nait

, p. 13 - 16 (2001)

The first water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols have been developed. The catalytic system composed of [Ir(COD)Cl]2, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt (BQC) and sodium carbonate is highly efficient for the selective oxidation of benzylic and aliphatic secondary alcohols to the corresponding ketones with catalyst/substrate ratios ranging from 0.4 to 2.5 percent. The substitution of [Ir(COD)Cl]2 by its rhodium analog [Rh(COD)Cl]2 generates a less active catalytic system. [Ir(COD)Cl]2/BQC was also found to be more active than its water-insoluble analog system [Ir(COD)Cl]2/2,2'-biquinoline (BC).

A Mild and Efficient Oxidation of Alcohols to Ketones with Iodosobenzene/(Salen) Manganese Complex

Kim, Sung Soo,Borisova, Galina

, p. 3961 - 3967 (2003)

An excellent method for the chemoselective oxidation of alcohols to ketones with C6H5IO catalyzed by (salen) manganese/4A MS in CH3CN has been devised. The reported procedure is fast, simple, and the yields are excellent (> 95%) in most cases.

TEMPO-tert-butyl nitrite: An efficient catalytic system for aerobic oxidation of alcohols

He, Xijun,Shen, Zhenlu,Mo, Weimin,Sun, Nan,Hu, Baoxiang,Hu, Xinquan

, p. 89 - 92 (2009)

A metal-free catalytic system consisting of 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and tert-butyl nitrite has been developed to activate molecular oxygen for the aerobic oxidation of alcohols. A variety of active and non-active alcohols were oxidized to their corresponding carbonyl compounds in high selectivity and yields.

Enantiocomplementary C–H Bond Hydroxylation Combining Photo-Catalysis and Whole-Cell Biocatalysis in a One-Pot Cascade Process

Peng, Yongzhen,Li, Danyang,Fan, Jiajie,Xu, Weihua,Xu, Jian,Yu, Huilei,Lin, Xianfu,Wu, Qi

, p. 821 - 825 (2020)

Enantiocomplementary hydroxylation of alkyl aromatics through a one-pot photo-biocatalytic cascade reaction is described. The photoredox process is implemented in aqueous phase with O2 as oxidant and the subsequent (R)- or (S)-selective bioreduction is performed by whole cell system without the addition of the expensive cofactor (NADPH). This mild, operationally simple protocol transforms a wide variety of readily available aromatic compounds into valuable chiral alcohols with high yield (up to 90 %) and stereoselectivity (up to 99 %), thereby displaying important potentials in organic synthesis.

Catalytic Friedel-Crafts acylation of alkoxybenzenes mediated by aluminum hydrogensulfate in solution and solvent-free conditions

Salehi, Peyman,Khodaei, Mohammad Mehdi,Zolfigol, Mohammad Ali,Sirouszadeh, Sara

, p. 1863 - 1864 (2003)

Friedel-Crafts acylation of alkoxybenzenes was achieved efficiently by a reaction with aliphatic acid anhydrides in the presence of catalytic amounts of aluminum hydrogensulfate, Al(HSO4)3, in nitromethane and under solvent-free conditions. Alkylbenzenes and aryl halides, as well as aromatic anhydrides, remained intact under these conditions.

A Novel Catalyst System, Antimony(V) Chloride-Lithium Perchlorate (SbCl5-LiClO4), in the Friedel-Crafts Acylation Reaction

Mukaiyama, Teruaki,Suzuki, Kaoru,Han, Jeong Sik,Kobayashi, Shu

, p. 435 - 438 (1992)

A novel catalyst system consisting of antimony(V) chloride (SbCl5) and lithium perchlorate (LiClO4) effectively promotes the Friedel-Crafts acylation reaction of aromatic compounds with acid anhydrides.

A supported manganese complex with amine-bis(phenol) ligand for catalytic benzylic C(sp3)-H bond oxidation

Karimpour, Touraj,Safaei, Elham,Karimi, Babak

, p. 14343 - 14351 (2019)

With regards to the importance of direct and selective activation of C-H bonds in oxidation processes, we develop a supported manganese amine bis(phenol) ligand complex as a novel catalyst with the aim of obtaining valuable products such as carboxylic acids and ketones that have an important role in life, industry and academic laboratories. We further analyzed and characterized the catalyst using the HRTEM, SEM, FTIR, TGA, VSM, XPS, XRD, AAS, and elemental analysis (CHN) techniques. Also, the catalytic evaluation of our system for direct oxidation of benzylic C-H bonds under solvent-free condition demonstrated that the heterogeneous form of our catalyst has high efficiency in comparison with homogeneous ones due to more stability of the supported complex. Furthermore, the structural and morphological stability of our efficient recyclable catalytic system has been investigated and all of the data proved that the complex was firmly anchored to the magnetite nanoparticles.

N- Hydroxyphthalimide and transition metal salts as catalysts of the liquid-phase oxidation of 1-methoxy-4-(1-methylethyl)benzene with oxygen

Orlinska, Beata,Romanowska, Iwona

, p. 670 - 676 (2011)

The oxidation process of 1-methoxy-4-(1-methylethyl)benzene catalysed by N-hydroxyphthalimide (NHPI) or NHPI in combination with Cu(II), Co(II), Mn(II) and Fe(II) salts was studied. The effects of the amount of catalyst and the temperature were determined

Solid state cleavage of oximes with potassium permanganate supported on alumina

Imanzadeh,Hajipour,Mallakpour

, p. 735 - 740 (2003)

A manipulatively simple and rapid method for conversion of oximes to the corresponding carbonyl compounds is described. The reaction is conducted under solvent-less conditions using alumina-supported permanganate. According to the reaction system and conditions used, different ketones and aldehydes are obtained in moderate and good yields.

p-Methoxyphenacyl Esters as Photodeblockable Protecting Groups for Phosphates

Epstein, William W.,Garrossian, Massoud

, p. 532 - 533 (1987)

p-Methoxyphenacyl esters of substituted phosphates have been found to be photosensitive protecting groups which may be useful in biologically important phosphate synthesis.

Reactions of silica chloride (SiO2Cl)/DMSO, a heterogeneous system for the facile regeneration of carbonyl compounds from thioacetals and ring-expansion annelation of cyclic thioacetals

Firouzabadi, Habib,Iranpoor, Nasser,Hazarkhani, Hassan,Karimi, Babak

, p. 2572 - 2576 (2002)

Silica chloride (SiO2Cl)/DMSO, as a heterogeneous system, has been efficiently used for deprotection of thioacetals into aldehydes in dry CH2Cl2 at room temperature. Thioketals without enolizable hydrogens adjacent to a sulfur atom are converted easily to the corresponding ketones in high yields under similar reaction conditions. However, thioketals with enolizable methyl and methylene groups undergo ring-expansion reactions to afford 1,4-dithiepins and 1,4-dithiins in dry CH2Cl2 at room temperature in good yields.

VO(acac)2 catalyzed oxidative deprotection of oximes, hydrazones, and semicarbazones

De, Surya Kanta

, p. 4409 - 4415 (2004)

Oximes, hydrazones, and semicarbazones undergo facile deprotection in the presence of a catalytic amount of vanadyl acetylacetonate and hydrogen peroxide in acetone at room temperature.

Biphasic copper-catalyzed C–H bond activation of arylalkanes to ketones with tert-butyl hydroperoxide in water at room temperature

Hossain, Md. Munkir,Shyu, Shin-Guang

, p. 4252 - 4257 (2016)

A facile C–H bond activation of arylalkanes to their corresponding ketones catalyzed by copper salts using tert-butyl hydroperoxide as an oxidant in water at room temperature is described. Easy product separation, simple reaction procedures (without using base or phase transfer catalysis), and catalyst recycling make the catalytic system attractive. It is also active beyond activated benzylic methylene positions and could tolerate factionalized arylalkanes with diverse groups.

Three Pd-decavanadates with a controllable molar ratio of Pd to decavanadate and their heterogeneous aerobic oxidation of benzylic C-H bonds

Huang, Xianqiang,Li, Jikun,Shen, Guodong,Xin, Nana,Lin, Zhengguo,Chi, Yingnan,Dou, Jianmin,Li, Dacheng,Hu, Changwen

, p. 726 - 733 (2017)

By the combination of Pd-complexes and [V10O28]6-, three Pd-decavanadate compounds [Pd(NH3)4]3[V10O28]·8H2O (1), [Pd(deta)(H2O)]2(NH4)2[V10O28]·2H2O (2) (deta = diethylenetriamine) and [Pd(dpa)2](Hdpa)2(Et3NH)2[V10O28]·2H2O (3) (dpa = 2,2′-dipyridylamine) have been successfully synthesized and thoroughly characterized using single X-ray diffraction (SXRD), powder X-ray diffraction (PXRD), infrared spectroscopy (FT-IR) and elemental analyses (EA). Interestingly, in the three compounds, the molar ratios of Pd to decavanadate vary from 3:1 to 1:1 by changing N-ligands. The three Pd-decavanadates as heterogeneous catalysts are active in the aerobic oxidation of benzylic hydrocarbons under solvent-free conditions without adding any additives and co-catalysts. Moreover, compound 1 can be reused three times without losing its activity.

Hydration of aromatic alkynes catalyzed by a self-assembled hexameric organic capsule

La Sorella, Giorgio,Sperni, Laura,Ballester, Pablo,Strukul, Giorgio,Scarso, Alessandro

, p. 6031 - 6036 (2016)

The combination of a Br?nsted acid catalyst and a supramolecular organic capsule formed by the self-assembly of six resorcin[4]arene units efficiently promotes the mild hydration of aromatic alkynes to their corresponding ketones. The capsule provides a suitable nanoenvironment that favors protonation of the substrate and addition of water.

Hydration of terminal alkynes catalyzed by a water-soluble salen-Co(III) complex

Wang, Shoufeng,Miao, Chengxia,Wang, Wenfang,Lei, Ziqiang,Sun, Wei

, p. 1695 - 1700 (2014)

A water-soluble salen-Co(III) complex was studied as catalyst for hydration of terminal alkynes to methyl ketones in the presence of H2SO4 as a co-catalyst. The products were obtained with excellent yields using relatively low catalyst loadings and a simple protocol. Notably, the products were easily separated from the catalyst after reaction by extraction, and the catalyst could be recovered and reused with only a slight loss of activity.

A well-defined complex for palladium-catalyzed aerobic oxidation of alcohols: Design, synthesis, and mechanistic considerations

Jensen, David R.,Schultz, Mitchell J.,Mueller, Jaime A.,Sigman, Matthew S.

, p. 3810 - 3813 (2003)

A breath of fresh air: A variety of alcohols are oxidized using 0.5-0.1 mol% of the catalyst, and in some cases the oxidation can simply be carried out open to the air (see scheme). Mechanistic insight into the mechanism is provided by a crystal structure that shows remarkable hydrogen bonds between the coordinated water and acetate ligands and an unprecedented large kinetic isotope effect.

Identification of an ASE2 Mechanism in the Hydrolysis of Cyclic Thioacetals

Ali, Muhammad,Satchell, Derek P. N.

, p. 866 - 867 (1991)

2-Phenyl-2-methyl-1,3-dithiane and its p-methoxy derivative undergo hydrolysis in concentrated aqueous perchloric acid via the ASE2 mechanism rather than via the A1 mechanism.

Ruthenium carbonyl complexes with pyridine-alkoxide ligands: Synthesis, characterization and catalytic application in dehydrogenative oxidation of alcohols

Hao, Zhiqiang,Yan, Xinlong,Liu, Kang,Yue, Xiaohui,Han, Zhangang,Lin, Jin

, p. 15472 - 15478 (2018)

Several new trinuclear ruthenium carbonyl complexes chelated with 6-bromopyridine alcohol ligands, [6-bromopyC(CH2)4O]Ru3(CO)9 (1a), [6-bromopyC(CH2)5O]Ru3(CO)9 (1b), [6-bromopyC(Me)2O]Ru3(CO)9 (1c) and [6-bromopyCMeC6H5O]Ru3(CO)9 (1d), were synthesized by the reaction of Ru3(CO)12 with 6-bromopyC(CH2)4OH (L1H), 6-bromopyC(CH2)5OH (L2H), 6-bromopyC(Me)2OH (L3H) and 6-bromopyCMeC6H5OH (L4H) in refluxing THF, respectively. The free ligands L1H-L4H were synthesized by the nucleophilic reaction of lithium salt (generated from 2,6-dibromopyridine and n-BuLi) with the corresponding ketones. Furthermore, these pyridine-based ligands were characterized by NMR spectroscopy and elemental analyses. All the four ruthenium carbonyl complexes were well characterized by NMR, IR, single-crystal X-ray crystallography, etc. Complexes 1a-1d were found to exhibit high catalytic activities for the dehydrogenative oxidation of secondary alcohols to give their corresponding products in good to excellent yields.

-

Kosolapoff

, p. 1651 (1947)

-

Rh- and Ru-complex-catalyzed dimerization of arylethynes Rylethynes in aqueous environment

Novak, Petr,Kotora, Martin

, p. 433 - 442 (2009)

Complexes [RhCl(PPh3)3] and [Ru(CHPh)Cl 2(PCy3)2] efficiently catalyzed the dimerization of arylethynes to the corresponding 1,4-substituted enynes in aqueous environment in the presence of sodium dodecyl sulfate. The Rh catalyst exhibited almost exclusive preference for the formation of £-isomers, the Ru one exhibits strong preference for the formation of Z-isomers.

Light-driven carbon dioxide reduction coupled with conversion of acetylenic group to ketone by a functional Janus catalyst based on keplerate {Mo132}

Lodh, Joyeeta,Mallick, Apabrita,Roy, Soumyajit

, p. 20844 - 20851 (2018)

Catalysts enabling CO2 reduction coupled with another organic reaction are rare. In this study, we report such a catalyst keplerate {Mo132}, which catalyses photochemical carbon dioxide reduction to formic acid coupled with organic transformation, i.e., hydration of phenylacetylene to acetophenone in visible light. It initially oxidizes water and injects the reducing equivalents for reduction of carbon dioxide at the same time, converting acetylenic group to ketone. Our designed redox Janus catalyst provides an inexpensive pathway to achieve carbon dioxide reduction as well as conversion of phenylacetylene to acetophenone, which is an industrially important precursor.

Highly efficient oxidation of alcohols catalyzed by a porphyrin-inspired manganese complex

Dai, Wen,Lv, Ying,Wang, Lianyue,Shang, Sensen,Chen, Bo,Li, Guosong,Gao, Shuang

, p. 11268 - 11271 (2015)

A novel strategy for catalytic oxidation of a variety of benzylic, allylic, propargylic, and aliphatic alcohols to the corresponding aldehydes or ketones by an in situ formed porphyrin-inspired manganese complex in excellent yields (up to 99%) has been successfully developed.

Pd(II)-Mediated Oxidation of Olefine Using the Transannular Ozonides of 9-tert-Butylanthracenes as an Oxygen Atom Source

Matsuura, Akira,Ito, Yoshikatsu,Matsuura, Teruo

, p. 5002 - 5004 (1985)

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Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis

Li, Han,Wenger, Oliver S.

supporting information, (2021/12/23)

The two-electron reduced forms of perylene diimides (PDIs) are luminescent closed-shell species whose photochemical properties seem underexplored. Our proof-of-concept study demonstrates that straightforward (single) excitation of PDI dianions with green

Copper-Catalyzed Azide-Alkyne Cycloaddition of Hydrazoic Acid Formed in Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles

Jankovi?, Dominik,Virant, Miha,Gazvoda, Martin

, p. 4018 - 4028 (2022/02/25)

We report a copper-catalyzed cycloaddition of hydrogen azide (hydrazoic acid, HN3) with terminal alkynes to form 4-substituted-1H-1,2,3-triazoles in a sustainable manner. Hydrazoic acid was formed in situ from sodium azide under acidic conditions to react with terminal alkynes in a copper-catalyzed reaction. Using polydentate N-donor chelating ligands and mild organic acids, the reactions were realized to proceed at room temperature under aerobic conditions in a methanol-water mixture and with 5 mol % catalyst loadings to afford 4-substituted-1,2,3-triazoles in high yields. This method is amenable on a wide range of alkyne substrates, including unprotected peptides, showing diverse functional group tolerance. It is applicable for late-stage functionalization synthetic strategies, as demonstrated in the synthesis of the triazole analogue of losartan. The preparation of orthogonally protected azahistidine from Fmoc-l-propargylglycine was realized on a gram scale. The hazardous nature of hydrazoic acid has been diminished as it forms in situ in a reactive species in the copper-catalyzed reaction.

Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides

Li, Tingting,Hammond, Gerald B.,Xu, Bo

supporting information, p. 9737 - 9741 (2021/05/31)

A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C?C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.

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