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119-53-9

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119-53-9 Usage

Description

2-Hydroxy-2-phenylacetophenone, also known as benzoin, is a ketone consisting of acetophenone bearing hydroxy and phenyl substituents at the alpha-position. It is an off-white to yellow-white crystalline solid with an odor of camphor and a slightly acrid taste. When broken, the fresh surfaces have a milky-white color. Benzoin is a condensation product of benzenecarbaldehyde (benzaldehyde), made by the action of sodium cyanide on benzenecarbaldehyde in an alcoholic solution. It also occurs naturally as the resin of a tropical tree. It is both a secondary alcohol and a ketone, giving reactions characteristic of both types of compounds.

Uses

Used in Flavor Industry:
2-Hydroxy-2-phenylacetophenone is used as a flavoring agent for its spicy, balsamic, resinous, and fruity taste with an herbal nuance. It is particularly useful in the creation of various fragrances and flavors in the food and beverage industry.
Used in Pharmaceutical Industry:
2-Hydroxy-2-phenylacetophenone is used as an antiseptic due to its bactericidal properties, making it a valuable component in the development of pharmaceutical products for wound care and infection prevention.
Used in Photopolymerization Industry:
2-Hydroxy-2-phenylacetophenone is used as a photopolymerization catalyst, playing a crucial role in the production of various polymers and coatings.
Used in Organic Synthesis:
2-Hydroxy-2-phenylacetophenone serves as a raw material in organic syntheses, particularly in the production of benzil, which is a photoinitiator.
Used in Degassing for Powder Coatings:
2-Hydroxy-2-phenylacetophenone is used as a degassing agent for powder coatings, helping to remove the pinhole phenomenon and improve the overall quality of the finished product.
Used in Cosmetics Industry:
2-Hydroxy-2-phenylacetophenone is used as an additive in the cosmetics industry, where it is valued for its anti-irritation and anti-itching properties, as well as its ability to reduce skin redness.
Used in Fragrance Industry:
2-Hydroxy-2-phenylacetophenone is used as a fragrant essential oil, extracted from the trees of the genus Styrax, primarily found in Indonesia and Thailand. Its camphor-like odor and sweet, balsamic scent make it a popular choice for creating various fragrances.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Hydroxy-2-phenylacetophenone is sensitive to heat and light. 2-Hydroxy-2-phenylacetophenone is incompatible with oxidizers. 2-Hydroxy-2-phenylacetophenone reduces Fehling's solution.

Hazard

Highly toxic.

Fire Hazard

Flash point data for 2-Hydroxy-2-phenylacetophenone are not available; however, 2-Hydroxy-2-phenylacetophenone is probably combustible.

Safety Profile

Slightly toxic by ingestion andskin contact. Mutation data reported. A flammable liquid.When heated to decomposition it emits acrid smoke andirritating fumes.

Synthesis

It may be prepared by condensation of benzaldehyde with an alkali cyanide and used in organic synthesis.

Purification Methods

Crystallise benzoin from CCl4, hot EtOH (8mL/g), or 50% acetic acid. Also crystallise it from high purity *benzene, then twice from high purity MeOH, to remove fluorescent impurities [Elliott & Radley Anal Chem 33 1623 1961]. It can be sublimed. [Beilstein 8 IV 1279.]

Check Digit Verification of cas no

The CAS Registry Mumber 119-53-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 9 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 119-53:
(5*1)+(4*1)+(3*9)+(2*5)+(1*3)=49
49 % 10 = 9
So 119-53-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H

119-53-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A10188)  Benzoin, 99%   

  • 119-53-9

  • 100g

  • 131.0CNY

  • Detail
  • Alfa Aesar

  • (A10188)  Benzoin, 99%   

  • 119-53-9

  • 250g

  • 300.0CNY

  • Detail
  • Alfa Aesar

  • (A10188)  Benzoin, 99%   

  • 119-53-9

  • 1000g

  • 500.0CNY

  • Detail
  • Alfa Aesar

  • (A10188)  Benzoin, 99%   

  • 119-53-9

  • 5000g

  • 2188.0CNY

  • Detail
  • Aldrich

  • (B8681)  Benzoin  98%

  • 119-53-9

  • B8681-100G

  • 312.39CNY

  • Detail
  • Aldrich

  • (B8681)  Benzoin  98%

  • 119-53-9

  • B8681-500G

  • 794.43CNY

  • Detail

119-53-9SDS

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 Benzoin

1.2 Other means of identification

Product number -
Other names BENZOIN GUM

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:119-53-9 SDS

119-53-9Synthetic route

benzaldehyde
100-52-7

benzaldehyde

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With triethylamine; 4,5-dimethylthiazole bound on chloromethylated polystyrene copolymer In ethanol for 12h; Ambient temperature;100%
With thiazolium iodide Mechanism; Product distribution; different thiazolium salts;100%
With 3,3'- (dodecane-1,12-diyl)bis(1-methyl-1H-benzo[d]imidazol-3-ium) dibromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 0.5h;100%
benzil
134-81-6

benzil

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With titanium(III) chloride In acetone at 0℃; for 1h;100%
Stage #1: benzil With sodium tetrahydroborate at 70℃; for 1.5h; Ball milling; neat (no solvent);
Stage #2: With water regiospecific reaction;
100%
With hydrogen; palladium In methanol at 20℃; under 3800 Torr; for 46h;98%
2-hydroxy-1,2,3-triphenyl-propan-1-one
7540-93-4

2-hydroxy-1,2,3-triphenyl-propan-1-one

A

phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran for 1h; Heating;A 100%
B 38%
C 6%
α-(2-cyanoethyl)benzoin
174869-02-4

α-(2-cyanoethyl)benzoin

A

4-oxo-4-phenylbutanenitrile
5343-98-6

4-oxo-4-phenylbutanenitrile

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran for 1h; Ambient temperature;A 100%
B 75%
C 2%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With C7H7N2O4(1-)*NO3(1-)*Pb(2+); potassium tert-butylate In toluene at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;98.75%
1,2-diphenyl-2-(trimethylsilyloxy)ethanone
26205-39-0

1,2-diphenyl-2-(trimethylsilyloxy)ethanone

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry;98%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;96%
With aminosulfonic acid; water at 20℃; for 8h;92%
With benzyltriphenylphosphonium tribromide In methanol at 20℃; for 0.05h;90%
With K5 In acetonitrile at 20℃; for 0.5h;100 % Chromat.
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With Merrifield's resin-bound N-aminoimidazolium chlorochromate In dichloromethane for 24h; Heating;96%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; tert.-butylnitrite; oxygen In 1,2-dichloro-ethane under 1500.15 Torr; for 12h; Autoclave; Heating;95%
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 80℃; under 1500.15 Torr; for 15h; Autoclave;95%
bis(η5-cyclopentadienyl)titana-2,5-dioxa-3,4-diphenyl-cyclopent-3-ene

bis(η5-cyclopentadienyl)titana-2,5-dioxa-3,4-diphenyl-cyclopent-3-ene

A

bis(cyclopentadienyl)titanium dichloride
1271-19-8

bis(cyclopentadienyl)titanium dichloride

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With chloro-trimethyl-silane; waterA n/a
B 95%
benzoin oxime

benzoin oxime

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With water; Dess-Martin periodane In dichloromethane at 5 - 20℃; for 0.333333h;94%
With N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide) In tetrachloromethane at 20℃; for 2h; Product distribution;90%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.366667h;90%
Conditions
ConditionsYield
With oxone; sodium hydrogencarbonate; ruthenium trichloride In water; ethyl acetate; acetonitrile at 20℃; for 0.166667h;94%
With oxone; sodium hydrogencarbonate; ruthenium trichloride In water; ethyl acetate; acetonitrile at 20℃; for 0.166667h;91%
benzaldehyde
100-52-7

benzaldehyde

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
185990-03-8

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In water Reagent/catalyst; Benzoin Condensation; enantioselective reaction;94%
benzaldehyde
100-52-7

benzaldehyde

C68H93N6O7S(1+)*3Cl(1-)*2H(1+)

C68H93N6O7S(1+)*3Cl(1-)*2H(1+)

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With triethylamine In d(4)-methanol at 49.9℃; for 12h; Rate constant; different solvent, educt and product; H/D-exchange experiments;93%
benzoin tetrahydropyranyl ether
51706-34-4

benzoin tetrahydropyranyl ether

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With Montmorillonite KSF In methanol at 40 - 50℃; for 1h;93%
With iron(III) phosphate In methanol at 20℃; for 3h;82 %Chromat.
1,2-diphenyl-2-triethylsilyloxyethanone
13959-93-8

1,2-diphenyl-2-triethylsilyloxyethanone

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With potassium fluoride; Tetraethylene glycol at 20℃; for 2h; chemoselective reaction;93%
With hydrogenchloride; water In methanol at 20℃; for 0.166667h; Inert atmosphere;
C17H20O2Si

C17H20O2Si

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3.5h; Microwave irradiation;93%
(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With bromine; oxygen; dimethyltin dichloride; potassium carbonate In water at 50℃; for 1h; Darkness; Green chemistry;92%
With dihydroxy-methyl-borane; potassium carbonate; dibromoisocyanuric acid In water at 50℃; for 7h; Reagent/catalyst; Darkness; Electrochemical reaction; Green chemistry;87%
With iodine(V) reagent In acetonitrile at 20 - 65℃; for 4h;79%
With (2-iodoxyphenyl)acetic acid methyl ester; trifluoroacetic acid In acetonitrile at 20℃; for 4h;100 %Spectr.
Diethyl 2-hydroxy-1-(trimethylsiloxy)-1,2-diphenylethanephosphonate
74552-49-1

Diethyl 2-hydroxy-1-(trimethylsiloxy)-1,2-diphenylethanephosphonate

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With sodium hydroxide for 0.333333h; Ambient temperature;91%
(1-Oxo-2-phenyl-1,2-dihydro-1λ4-naphtho[1,8-de][1,3]dithiin-2-yl)-phenyl-methanol

(1-Oxo-2-phenyl-1,2-dihydro-1λ4-naphtho[1,8-de][1,3]dithiin-2-yl)-phenyl-methanol

A

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

B

1,8-naphthalenedisulfide
209-22-3

1,8-naphthalenedisulfide

Conditions
ConditionsYield
In benzene for 20h; Ambient temperature; Irradiation;A 83%
B 91%
benzaldehyde
100-52-7

benzaldehyde

A

1,2-diphenyl-2-oxoethyl benzoate
1459-20-7

1,2-diphenyl-2-oxoethyl benzoate

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With C43H48N6(2+)*2Br(1-); potassium tert-butylate In toluene at 20℃; for 20h; Catalytic behavior; Reagent/catalyst; Solvent; Benzoin Condensation; Inert atmosphere; Schlenk technique;A 8%
B 91%
With 1-butyl-3-methylimidazolium hydroxide; 1,3-dimethylbenzimidazolium Iodide at 20 - 80℃; Benzoin Condensation;A 7%
B 87%
With 1,3-dimethylbenzimidazolium Iodide; 4-nitro-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 1h; Heating;A 48%
B 7%
benzophenone
119-61-9

benzophenone

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With samarium; chloro-trimethyl-silane at 90℃; for 10h;91%
cis-stilben
645-49-8

cis-stilben

A

(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide; polyaniline-supported Os In water; acetone; acetonitrile at 20℃; for 3h;A 91%
B n/a
C n/a
methyl 3-bromo-2-oxo-4-phenylbutanoate

methyl 3-bromo-2-oxo-4-phenylbutanoate

benzaldehyde
100-52-7

benzaldehyde

A

methyl (2S,3S)-2-benzoyl-3-bromo-2-hydroxy-4-phenylbutanoate

methyl (2S,3S)-2-benzoyl-3-bromo-2-hydroxy-4-phenylbutanoate

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With BF4(1-)*C21H22N3O(1+); potassium carbonate In tert-butyl methyl ether at 20℃; for 14h; diastereoselective reaction;A 91%
B 9%

A

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Product distribution; Heating; effect of various chromium(VI) based oxidants;A 10%
B 90%
benzoin phenylhydrazone ethyl ether
64357-12-6

benzoin phenylhydrazone ethyl ether

A

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

B

2-ethoxy-1,2-diphenyl-ethanone
574-09-4

2-ethoxy-1,2-diphenyl-ethanone

C

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

D

benzaldehyde
100-52-7

benzaldehyde

E

chlorobenzene
108-90-7

chlorobenzene

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
With copper dichloride for 5h; Product distribution; Heating; variation of time;A 90%
B 10%
C 40%
D 10%
E n/a
F n/a
benzoyltrimethylsilane
5908-41-8

benzoyltrimethylsilane

benzaldehyde
100-52-7

benzaldehyde

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h; Inert atmosphere; Irradiation; Schlenk technique;90%
With tetrabutyl ammonium fluoride In tetrahydrofuran50%
2-(α-hydroxybenzyl)-2-phenyl-1,3-dithiane
120046-05-1

2-(α-hydroxybenzyl)-2-phenyl-1,3-dithiane

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide In acetonitrile at 25℃; for 1h;90%
With thallium(III) trifluoroacetate for 0.5h; Ambient temperature;77%
DL-1,2-diphenylethane-1,2-diol
655-48-1

DL-1,2-diphenylethane-1,2-diol

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With dihydroxy-methyl-borane; potassium carbonate; dibromoisocyanuric acid In water at 50℃; for 7h; Darkness; Electrochemical reaction; Green chemistry;89%
With pyridine; phenyltrimethylammonium tribromide; copper(ll) bromide In methanol at 20℃; for 72h;54%
With nitric acid; acetic acid dl-benzoin;
With nitric acid dl-benzoin;
(R,R)-hydroxybenzoin
52340-78-0

(R,R)-hydroxybenzoin

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With bromine; oxygen; dimethyltin dichloride; potassium carbonate In water at 50℃; for 1h; Darkness; Green chemistry;89%
benzaldehyde
100-52-7

benzaldehyde

benzoyl chloride
98-88-4

benzoyl chloride

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran for 0.00833333h; Ambient temperature;86%
With hydrogenchloride; samarium diiodide In tetrahydrofuran for 2h; Ambient temperature;86%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

Conditions
ConditionsYield
With pyridine; iodine In toluene for 7h; Inert atmosphere; Reflux;100%
With titanium; pyrographite In tetrahydrofuran Heating;80%
With phosphorus; hydrogen iodide In water; toluene at 80℃; for 1h; Inert atmosphere;80%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

Conditions
ConditionsYield
With tricyclohexylphosphineindium trihydride In toluene at -78 - 20℃; for 15h;100%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.0833333h; Reduction;92%
With ethanol; nickel at 125℃; under 117681 Torr; Hydrogenation;
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With pyridine chromium peroxide In benzene for 0.1h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
With pyridine chromium peroxide In benzene for 0.1h; Heating;100%
With 4-dimethylaminopyridine tribromide In dichloromethane for 0.25h; Ambient temperature;100%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With magnesium(II) perchlorate; 3-(N,N-dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine In [D3]acetonitrile at 0℃; for 1h; Mechanism; also with (S)-benzoin and opt. active dihydropyridine; stereoselectivity;100%
With magnesium(II) perchlorate; 3-(N,N-dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine In [D3]acetonitrile at 0℃; for 1h; also with (R)-1;100%
With sodium tetrahydroborate In methanol at 0℃; for 1h;100%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
With hydrogen In ethanol at 39.84℃; under 760.051 Torr; for 5h;100%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h;96%
With sodium cyanoborohydride at 20℃; for 0.05h;95%
benzoyl cyanide
613-90-1

benzoyl cyanide

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

1,2-diphenyl-2-oxoethyl benzoate
1459-20-7

1,2-diphenyl-2-oxoethyl benzoate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; Molecular sieve;100%
In acetone at 65℃; for 7h;70%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

allyl alcohol
107-18-6

allyl alcohol

(1RS,2SR)-1,2-diphenyl-pent-4-ene-1,2-diol
56072-16-3, 122270-54-6

(1RS,2SR)-1,2-diphenyl-pent-4-ene-1,2-diol

Conditions
ConditionsYield
With tin(ll) chloride; bis(benzonitrile)palladium(II) dichloride In tetrahydrofuran at 25℃; for 68h;100%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

allyl bromide
106-95-6

allyl bromide

1,2-diphenyl-pent-4-ene-1,2-diol
56072-16-3

1,2-diphenyl-pent-4-ene-1,2-diol

Conditions
ConditionsYield
With copper; tin(ll) chloride In water at 20℃; for 8h;100%
With tin In tetrahydrofuran; water Ambient temperature; Irradiation;90%
With tin(ll) chloride; cobalt acetylacetonate In water at 20℃; for 18h; Barbier coupling reaction;89%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With NH-pyrazole; air; sodium hydride In tetrahydrofuran for 5h; Ambient temperature;100%
With iodopentafluorobenzene bis(trifluoroacetate) In water; benzene Mechanism;94%
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 48h;94%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

isobutyryl chloride
79-30-1

isobutyryl chloride

Isobutyric acid 2-oxo-1,2-diphenyl-ethyl ester

Isobutyric acid 2-oxo-1,2-diphenyl-ethyl ester

Conditions
ConditionsYield
With sulfuric acid; isobutyric Acid for 0.5h; Heating;100%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Z-D-proline
6404-31-5

Z-D-proline

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(2-oxo-1,2-diphenyl-ethyl) ester

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(2-oxo-1,2-diphenyl-ethyl) ester

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane100%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

2-oxo-1,2-diphenylethyl pivalate
51891-90-8

2-oxo-1,2-diphenylethyl pivalate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane for 2h;100%
With pyridine at 25℃; Inert atmosphere;91%
With triethylamine In dichloromethane at 20℃;
(-)-5(S)-(3-methoxybenzyl)-1-cyclopentenecarboxylic acid
171046-49-4

(-)-5(S)-(3-methoxybenzyl)-1-cyclopentenecarboxylic acid

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

(+)-(5S)-1-(4,5-diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopentene
171046-58-5

(+)-(5S)-1-(4,5-diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopentene

Conditions
ConditionsYield
With pyridine; ammonium acetate; thionyl chloride In hydrogenchloride; dichloromethane; ethyl acetate; N,N-dimethyl-formamide99.6%
Dimethoxymethane
109-87-5

Dimethoxymethane

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

α-<(methoxymethyl)oxy>benzyl phenyl ketone

α-<(methoxymethyl)oxy>benzyl phenyl ketone

Conditions
ConditionsYield
With Mo(VI)/ZrO2 at 40℃; for 0.333333h; Reflux; Inert atmosphere; Green chemistry;99.1%
With phosphorus pentoxide In chloroform at 0 - 20℃; for 4h;90%
acetic anhydride
108-24-7

acetic anhydride

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

2-acetoxy-2-phenylacetophenone
62398-10-1, 84275-45-6, 84275-46-7, 574-06-1

2-acetoxy-2-phenylacetophenone

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.0833333h;99%
With magnesium(II) perchlorate at 20℃; for 6h;99%
With m-nitrobenzene boronic acid at 20℃; for 17h;99%
propionyl chloride
79-03-8

propionyl chloride

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

α-propionyloxy-deoxybenzoin
53901-50-1

α-propionyloxy-deoxybenzoin

Conditions
ConditionsYield
With sulfuric acid; propionic acid for 0.5h; Heating;99%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

benzoic acid anhydride
93-97-0

benzoic acid anhydride

1,2-diphenyl-2-oxoethyl benzoate
1459-20-7

1,2-diphenyl-2-oxoethyl benzoate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.583333h; Heating;99%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

acetic acid
64-19-7

acetic acid

2-acetoxy-2-phenylacetophenone
62398-10-1, 84275-45-6, 84275-46-7, 574-06-1

2-acetoxy-2-phenylacetophenone

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 1h;99%
With K5 for 0.75h; Heating;97%
With poly(4-vinylpyridine) perchlorate In neat (no solvent) at 20℃; for 0.333333h;92%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

formic acid ethyl ester
109-94-4

formic acid ethyl ester

2-oxo-1,2-diphenylethyl formate
82027-51-8

2-oxo-1,2-diphenylethyl formate

Conditions
ConditionsYield
With K5 for 0.5h; Heating;99%
With bismuth(lll) trifluoromethanesulfonate for 1h; Heating;97%
With poly(4-vinylpyridinium tribromide) at 20℃; for 1.5h; neat (no solvent);64%
With polyvinylpolypyrrolidonium tribromide at 20℃; for 1.5h; Neat (no solvent);64%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

benzaldehyde
100-52-7

benzaldehyde

lophine
484-47-9

lophine

Conditions
ConditionsYield
With ammonium acetate; iodine In ethanol at 20℃; for 1h; Product distribution; Further Variations:; Temperatures; amount of I2;99%
With ammonium acetate; glycine at 100℃; for 0.333333h; neat (no solvent, solid phase);99%
With ammonium acetate at 20℃; for 0.2h;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole
5496-39-9

2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole

Conditions
ConditionsYield
With ammonium acetate at 20℃; for 0.216667h;99%
With P2O5/SiO2; ammonium acetate at 100℃; for 1.5h;95%
With triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate; ammonium acetate at 100℃; for 1.5h; neat (no solvent);95%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

ethylenediamine
107-15-3

ethylenediamine

2,3-diphenyl-5,6-dihydropyrazine
1489-06-1

2,3-diphenyl-5,6-dihydropyrazine

Conditions
ConditionsYield
With morpholine; iron(III) chloride In ethanol at 80℃; for 0.3h;99%
With [P4-VP]-PdNPs In N,N-dimethyl-formamide at 120℃; for 0.00833333h; Reflux;96%
With ammonium acetate at 80℃; for 1h; Green chemistry;94%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

2-nitro-aniline
88-74-4

2-nitro-aniline

A

2,3-diphenylquinoxaline
1684-14-6

2,3-diphenylquinoxaline

B

benzil
134-81-6

benzil

Conditions
ConditionsYield
With sodium hydroxide In toluene at 120℃; for 3h; Inert atmosphere; Sealed tube;A 99%
B 50%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

A

dimethylsulfide
75-18-3

dimethylsulfide

B

benzil
134-81-6

benzil

Conditions
ConditionsYield
With antimonypentachloride; dimethyl sulfoxide In nitromethane; benzene for 2h; Heating;A n/a
B 98.7%
1-amino-naphthalene
134-32-7

1-amino-naphthalene

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

α-[1]naphthylamino-deoxybenzoin

α-[1]naphthylamino-deoxybenzoin

Conditions
ConditionsYield
With acetic acid at 110℃; for 0.5h;98%
With tin(II) chloride dihdyrate at 80℃; for 2.5h;90%
With iodine at 130℃;

119-53-9Relevant articles and documents

THE REACTION OF PHENYLLITHIUM WITH CARBON MONOXIDE

Nudelman, N. Sbarbati,Vitale, Arturo A.

, p. 143 - 156 (1983)

Three main products are obtained from the reaction between phenyllithium and carbon monoxide, namely: benzophenone (I), benzoin (II) and α,α-diphenylacetophenone (III).Evidence is given for the existence of benzoyllithium as the first intermediate of the reaction and for the subsequent intermediates in the production of I, II and III.The basic sequences followed in the formation of those and of other minor products are outlined in the Scheme.Reaction conditions can be adjusted to obtain III in a high yield or to prevent further reaction of the first intermediate and obtain diarylalkylcarbinols, or substituted tetrahydrofurans.

Photocatalytic Coproduction of Deoxybenzoin and H2 through Tandem Redox Reactions

Luo, Nengchao,Hou, Tingting,Liu, Shiyang,Zeng, Bin,Lu, Jianmin,Zhang, Jian,Li, Hongji,Wang, Feng

, p. 762 - 769 (2020)

Photocatalytic H2 evolution from organic feedstocks with simultaneous utilization of photogenerated holes achieves solar energy storage and coproduces value-Added chemicals. Here we show visible-light H2 production from benzyl alcohol (BAL) with controllable generation of deoxybenzoin (DOB) or benzoin (BZ) through tandem redox reactions. Particularly, DOB synthesis circumvents the use of expensive feedstocks and environmentally unfriendly catalysts that are required previously. Under the irradiation of blue LEDs, the key of steering the major product to DOB rather than BZ is to decrease the conduction band bottom potentials of the ZnIn sulfide catalysts by increasing the Zn/In ratio, which results in the dehydration of intermediate hydrobenzoin (HB) to DOB proceeding in a redox-neutral mechanism and consuming an electron-hole pair. As a proof of concept, this method is used to synthesize DOB derivatives in gram scale.

-

Ohnishi,Kagami

, p. 2437 (1975)

-

-

Tanaka et al.

, p. 4979 (1972)

-

Pyridinium dichromate-assisted oxidative cleavage of α-functionalized benzylic alcohols by sodium percarbonate under phase-transfer conditions

Mohand,Levina,Muzart

, p. 2051 - 2059 (1995)

The course and the efficacy of the oxidation by sodium percarbonate of benzylic alcohols, α-substituted by a keto, hydroxy, ester or acid group, are dependent on the nature of both α-group and the solvent, and yields are usually improved by the presence of catalytic amounts of Cr(VI) species. The oxidative cleavage of the C(OH)-C(α) bond is the main process observed.

Postulation of Bis(thiazolin-2-ylidene)s as the Catalytic Species in the Benzoin Condensation Catalyzed by a Thiazolium Salt plus Base

Castells, J.,Lopez-Calahorra, F.,Domingo, L.

, p. 4433 - 4436 (1988)

Thiazolin-2-ylidenes generated by desilylation of 2-(trimethylsilyl)thiazolium ions are used as catalysts for the benzoin condensation.The experimental results together with theoretical calculations lead the postulate that bis(thiazolin-2-ylidene)s, and n

On the reactivity and stability of electrogenerated N-heterocyclic carbene in parent 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate: Formation and use of N-heterocyclic carbene-CO2 adduct as latent catalyst

Feroci, Marta,Chiarotto, Isabella,Vecchio Ciprioti, Stefano,Inesi, Achille

, p. 95 - 101 (2013)

A simple electrolysis (under galvanostatic conditions) of the room temperature ionic liquid 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate, BMIm-BF4, yields, after bubbling CO2 into the catholyte, theadduct NHC-CO2. The considerable stability of this NHC-CO 2 adduct, at room temperature, in the parentionic liquid as solvent, has been compared with the one of free NHC in the same BMIm-BF4. The BMIm-BF4solution containing NHC-CO2 adduct, suitably triggered (US irradiation or 120 °C), is able to releasefree NHC. The NHC-CO2 adduct usefulness has been demonstrated using it as efficient latent catalyst, inBMIm-BF4as solvent, in the benzoin condensation and in the oxidative esterification of cinnamaldehydewith benzyl alcohol.

Reduction of Sulfur Dioxide and Carbon Dioxide with Benzoin Carbanion. Oxygen Transfer from Products Formed by the Reduction of Sulfur Dioxide to 7,7,8,8-Tetracyanoquinodimethane

Akiyama, Fuminori

, p. 3951 - 3956 (1988)

A reaction of sulfur dioxide (SO2) with benzoin carbanion (the lithium salt of benzoin dianion, 1) in tetrahydrofuran (THF) gave a mixture of benzyl (2) and benzoin (3) in yields of 83 and 17 percent, respectively, irrespective of the reaction temperature between -78 and 25 deg C.The reaction of carbon dioxide (CO2) with 1 in THF gave a mixture of 2 and 3 accompanied by the formation of a small amount of lithium benzoate (4).The proportion of 2 in a mixture of 2 and 3 formed in the reaction of CO2 with 1 were 49, 30, and 20percent at -78, -22, and 25 deg C, respectively.The reaction of SO2 with 1 in the presence of 7,7,8,8-tetracyanoquinodimethane (TCNQ) gave oligomers of TCNQ with a yield of 60percent, in which some parts of the cyano groups were transformed to carboxylato groups.

-

Solodar

, p. 287,289 (1971)

-

-

Nadkarni,Mehta

, p. 901 (1935)

-

Organocatalysis in polysiloxane gels: A magnetic-stir-bar encapsulated catalyst system prepared by thiol-ene photo-click immobilization

Yang, Hong,Xu, Ming,Guo, Ling-Xiang,Ji, Hao-Fan,Wang, Jun-Yu,Lin, Bao-Ping,Zhang, Xue-Qin,Sun, Ying

, p. 7304 - 7310 (2015)

This manuscript presents a facile thiol-ene photo-click chemistry method to prepare magnetic stir bar-encapsulated polysiloxane-based organocatalyst gels under benign conditions, and develops a Stir Bar-Encapsulated Catalysis (SBEC) technique. Through thiol-ene addition chemistry, we graft olefin-terminated organocatalysts (i.e. MacMillan catalyst, proline catalyst, and N-heterocyclic carbene catalyst) onto poly[3-mercaptopropylmethylsiloxane], which is further photo-crosslinked to coat the embedded magnetic stir bar. The prepared magnetic stir bar-encapsulated polysiloxane-based organocatalyst gels can be put into reaction flasks to perform stirring and catalysis functions at the same time. The most important benefit of SBEC technique is to infinitely simplify the catalyst/product separation procedure by using a simple stir-bar-retriever, even without any precipitation/filtration steps. The catalytic performances of three different organocatalyst gels applied in asymmetric Diels-Alder reaction, asymmetric aldol reaction and benzoin condensation reaction respectively are also examined herein.

Selective Aerobic Oxidation of Benzyl Alcohols with Palladium(0) Nanoparticles Suspension in Water

Bourbiaux, Dolorès,Mangematin, Stéphane,Djakovitch, Laurent,Rataboul, Franck

, p. 3239 - 3249 (2021)

Abstract: This study concerns one of the rare applications of a suspension of palladium nanoparticles in water for oxidation reactions. The aqueous suspension containing well dispersed nanoparticles of 3.85?nm was obtained following a straightforward procedure involving the reduction of Na2PdCl4 with NaBH4 in the presence of PVP as stabilizing agent. In the way of oxidative catalytic valorisation of lignin, the aqueous suspension was directly applied as catalytic medium for the selective oxidation of vanillic alcohol into vanillin (80?°C, O2, 1?h) with more than 90% yield. Reusability of the catalytic medium has been demonstrated, acting as “quasi-homogeneous catalyst”. More sophisticated lignin-derived substrates like veratryl alcohol and hydrobenzoin gave yields of 50–80% to the respective aldehyde and ketone. In parallel, this as-synthesized suspension was directly used to prepare a Pd/TiO2 catalyst, the latter showing less efficiency for the catalytic transformations. Graphic Abstract: [Figure not available: see fulltext.]

Photochemical Transformations of 1,2-Diketones and Benzhydrylamine

Mehrotra, Kailash Nath,Pandey, Ganesh Prasad

, p. 1081 - 1084 (1980)

Photolysis of a mixture of substituted 1,2-diketones and benzhydrylamine (in 1:2 mole ratio) in benzene gave N-benzhydrylidenebenzhydrylamine, N-(diarylmethyl)benzamides, acyloins (3), N-(arylmethylene)benzhydrylamines, and benzophenone separated by fractional crystallization and column chromatogaphy.The products have been characterised by analytical and spectral (IR, UV, and NMR) data and the structural assignments confirmed by the comparison (IR spectra and undepressed mixed mp) with authentic samples.Acyloins (3) are precursors for N-(diarylmethyl)benzamides and N-(arylmethylene)benzhydrylamines.A tentative mechanistic route for the formation of products has been suggested.

Reductive formation and transformation of epoxides in neutral aqueous medium

Kovacs, Gabor,Micskei, Karoly

, p. 9055 - 9056 (1997)

Stoichiometrically controlled reductive epoxidation could be elaborated to transform α,β-diketones or α-hydroxy ketones to epoxides in a very good yields in neutral aqueous medium using chromium(II)acetate. Modification of the coordination sphere of Cr(II) ion with the added ligand makes the reductive ring-opening possible.

Samarium diiodide promoted formation of 1,2-diketones and 1-acylamido-2-substituted benzimidazoles from N-acylbenzotriazoles

Wang, Xiaoxia,Zhang, Yongmin

, p. 4201 - 4207 (2003)

N-Acylbenzotriazoles, when treated with samarium diiodide in THF, undergo self-coupling reaction to afford 1,2-diketones in good to excellent yields; while when treated with samarium diiodide in CH3CN, they undergo ring-opening reaction to afford 1-acylamido-2-alkyl (or aryl) benzimidazoles in reasonable to good yields. A plausible mechanism was suggested.

A γ-CYCLODEXTRIN THIAZOLIUM SALT HOLOENZYME MIMIC FOR THE BENZOIN CONDENSATION

Breslow, Ronald,Kool, Eric

, p. 1635 - 1638 (1988)

Several thiazolium salts have been attached to a C-6 carbon of γ-cyclodextrin.They catalyze the benzoin condensation of benzaldehyde very effectively.

Solid-support-bound 1-aminoimidazolium chlorochromate: A selective, efficient and recyclable oxidant

Linares,Sánchez,Alajarín,Vaquero,Alvarez-Builla

, p. 382 - 388 (2001)

A series of polymer-bound imidazolium chlorochromates have been synthesised and used as selective oxidants for benzylic and cinnamylic alcohols. Solid-support-bound 1-amino-imidazolium chlorochromate proved to be the most convenient system due to its efficiency, selectivity and ease of recycling the material.

N-Heterocyclic olefins as ancillary ligands in catalysis: A study of their behaviour in transfer hydrogenation reactions

Iturmendi, Amaia,García, Nestor,Jaseer,Munárriz, Julen,Sanz Miguel, Pablo J.,Polo, Victor,Iglesias, Manuel,Oro, Luis A.

, p. 12835 - 12845 (2016)

The Ir(i) complexes [Ir(cod)(κP,C,P′-NHOPPh2)]PF6 and [IrCl(cod)(κC-NHOOMe)] (cod = 1,5-cyclooctadiene, NHOPPh2 = 1,3-bis(2-(diphenylphosphanyl)ethyl)-2-methyleneimidazoline) and NHOOMe = 1,3-bis(2-(methoxyethyl)-2-methyleneimidazoline), both featuring an N-heterocyclic olefin ligand (NHO), have been tested in the transfer hydrogenation reaction; this representing the first example of the use of NHOs as ancillary ligands in catalysis. The pre-catalyst [Ir(cod)(κP,C,P′-NHOPPh2)]PF6 has shown excellent activities in the transfer hydrogenation of aldehydes, ketones and imines using iPrOH as a hydrogen source, while [IrCl(cod)(κC-NHOOMe)] decomposes throughout the reaction to give low yields of the hydrogenated product. Addition of one or two equivalents of a phosphine ligand to the latter avoids catalyst decomposition and significantly improves the reaction yields. The reaction mechanism has been investigated by means of stoichiometric studies and theoretical calculations. The formation of the active species ([Ir(κP,C,P′-NHOPPh2)(iPrO)]) has been proposed to occur via isopropoxide coordination and concomitant COD dissociation. Moreover, throughout the catalytic cycle the NHO moiety behaves as a hemilabile ligand, thus allowing the catalyst to adopt stable square planar geometries in the transition states, which reduces the energetic barrier of the process.

VIOLOGENS THAT PLUNDER ELECTRON FROM SOLID REDUCING AGENT. REDUCTION OF ARYL KETONES BY ZINC POWDER IN THE PRESENCE OF PROPYL VIOLOGEN AS AN ELECTRON TRANSFER CATALYST

Endo, Takeshi,Saotome, Yasushi,Okawara, Makoto

, p. 4525 - 4526 (1985)

It was found that viologen (propyl viologen) acted as an Electron Transfer Catalyst (ETC) in the reduction of aryl ketones with zinc powder. α-Diketones undertook the two-electron reduction to obtain the corresponding benzoins in good yields and aromatic ketones could one-electron reduced selectively to give the corresponding pinacols.

De Novo Synthesis of α-Hydroxy Ketones by Gallic Acid-Promoted Aerobic Coupling of Terminal Alkynes with Diazonium Salts

Alcaide, Benito,Almendros, Pedro,Fernández, Israel,Herrera, Fernando,Luna, Amparo

, p. 17227 - 17230 (2017)

An unprecedented metal-free direct preparation of unprotected α-hydroxy ketones from terminal alkynes under mild conditions with diazonium salts as the arene source and without the requirement of irradiation is described. The process is general and fully compatible with a wide variety of substitution in both reactants. Experimental and computational evidence strongly suggest the involvement of radical species in the transformation.

-

Baudry,Charpentier-Morize

, p. 3013 (1973)

-

One-pot synthesis benzils from aldehydes via nhc-catalyzed benzoin dimerization under metal-free conditions in water

Bi, Xiaoxin,Wu, Lintao,Yan, Chaoguo,Jing, Xiaobi,Zhu, Hongxiang

, p. 663 - 664 (2011)

A simple and convenient one-pot procedure is reported for the synthesis of 1,2-diketones from corresponding benzoin-type condensation reaction of aromatic aldehydes in water with N,N-dialkylbenzimidazolium salt as condensation catalyst and air as oxidizing reagent.

-

Merkushev,E.B. et al.

, (1978)

-

Metal-free porous phosphorus-doped g-C3N4photocatalyst achieving efficient synthesis of benzoin

Li, Yuanjin,Wang, Shuhui,Wu, Jin,Wang, Qiuyan,Ma, Changqiu,Jiang, Daheng,Hu, Wanglai,Zhu, Lixin,Xu, Xiaoliang

, p. 12682 - 12686 (2021)

Photocatalytic organic synthesis is mostly limited by the shortcomings of insufficient light absorption, high photogenerated electron-hole recombination rate and inadequate reactive sites of photocatalysts. To solve these problems, phosphorus-doped g-C3N4with a porous structure was constructed. Benefiting from enhanced light absorption and electron-hole separation efficiency, PCNT has intensive oxygen activation ability to generate superoxide radicals, and is highly active in organic synthesis. In addition, PCNT has enhanced surface nucleophilicity, which is conducive to the carbon-carbon coupling process of the intermediate product benzaldehyde molecules and benzyl alcohol molecules in the benzoin condensation reaction. Metal-free PCNT is expected to replace the previously used highly toxic cyanide catalysts and provide a new way for the low-cost and efficient photocatalytic synthesis of benzoin.

Synthesis, structure and oxidation of alkynes using a μ-oxo diiron complex with the ligand bis (1-(pyridin-2-ylmethyl)-benzimidazol-2-yl methyl) ether

Khattar, Raghvi,Hundal,Mathur, Pavan

, p. 129 - 134 (2012)

New ligand bis (1-(pyridin-2-ylmethyl)-benzimidazol-2-ylmethyl ether and its μ-oxo diferric complex has been synthesized and characterized. The dimeric [LClFe-O-FeCl3] has been characterized crystallographically, and shows that iron atoms occupy inequivalent coordination sites. One of the Fe (III) atom is coordinated by two benzimidazole nitrogens, one ether oxygen and bridging oxide oxygen, forming the equatorial plane while one Cl- ion and the oxygen atom of a DMF molecule occupy the axial fifth and the sixth coordination positions. The second Fe (III) is tetrahedrally coordinated by three Cl- ions and the bridging oxide oxygen O. The bridging oxide anion is unsymmerically coordinated to the two Iron (III) atoms. Oxidation of aromatic alkynes was investigated using this complex as catalyst with small amount of tert-butyl hydroperoxide (TBHP) and Hydrogen peroxide (H 2O2) as an alternate source of oxygen. Isolated products were characterized by GC-Mass. Solvent, temperature, Stoichiometry and oxidant variation are studied and reaction conditions have been optimized. Dicarbonyl and α,β-acetylenic ketone are the major product and depend on the nature of the alkyne employed.

Generation and reactivity of phenylhydroxycarbenes in solution

Keul, Felix,Mardyukov, Artur,Schreiner, Peter R.

supporting information, (2022/01/19)

We provide evidence for the first successful generation of phenylhydroxycarbene and 4-trifluoromethylphenylhydroxycarbene in solution. The carbene tautomers of the corresponding benzaldehyde derivatives had been prepared under cryogenic matrix-isolation conditions before but their reactivity, apart from a prototypical quantum mechanical tunneling [1,2]-H-shift reaction, had not been studied. Here our strategy is to employ suitable carbene precursors for the McFadyen–Stevens reaction, to generate the parent and the para-CF3-substituted phenylhydroxycarbenes, and to react them with benzaldehyde or acetone in a highly facile, allowed six-electron carbonyl-ene reaction toward the corresponding α-hydroxy ketones. Our findings are supported by computations at the DLPNO-CCSD(T)/cc-pVQZ//B3LYP/def2-TZVP level of theory.

Organocatalytic Synthesis of Substituted Vinylene Carbonates

Onida, Killian,Haddleton, Alice J.,Norsic, Sébastien,Boisson, Christophe,D'Agosto, Franck,Duguet, Nicolas

supporting information, p. 5129 - 5137 (2021/09/18)

The organocatalytic synthesis of substituted vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90 °C under solvent-free conditions. A wide range of substituted vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20–99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (>30 g after 5 runs). (Figure presented.).

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Badani, Purav,Chaturbhuj, Ganesh,Ganwir, Prerna,Misal, Balu,Palav, Amey

supporting information, (2021/06/03)

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

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