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102-16-9

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102-16-9 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 102-16-9 differently. You can refer to the following data:
1. Colorless liquid; honeylike odor.Soluble in alcohol. Combustible.
2. Benzyl phenylacetate has a sweet, floral (jasmine-rose) odor and a slight honey-like taste.

Occurrence

Not reported found in nature; phenylacetic acid, on the other hand, has been reported in several essential oils.

Uses

Perfumery and flavors.

Preparation

By direct esterification of benzyl alcohol with phenylacetic acid.

Synthesis Reference(s)

Synthesis, p. 138, 1982 DOI: 10.1055/s-1982-29718Tetrahedron Letters, 27, p. 55, 1986 DOI: 10.1016/S0040-4039(00)83938-6

General Description

Clear colorless liquid with a honey-like odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

BENZYL PHENYLACETATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. BENZYL PHENYLACETATE is sensitive to excessive light and heat.

Fire Hazard

BENZYL PHENYLACETATE is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 102-16-9 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 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 102-16:
(5*1)+(4*0)+(3*2)+(2*1)+(1*6)=19
19 % 10 = 9
So 102-16-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O2/c16-15(17)11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11H2,(H,16,17)/p-1

102-16-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzyl Phenylacetate

1.2 Other means of identification

Product number -
Other names BENZYL PHENYLACETATE

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:102-16-9 SDS

102-16-9Synthetic route

phenylacetyl chloride
103-80-0

phenylacetyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With samarium In acetonitrile at 70℃; for 0.0333333h;92%
With triethylamine In dichloromethane at 20℃; for 12h;70.1%
phenylacetic acid
103-82-2

phenylacetic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃;100%
With potassium carbonate In acetone Heating;99%
With hydrogen fluoride; mercury(II) oxide In 1,2-dichloro-ethane at 80℃; for 1h;79%
phenylacetic acid
103-82-2

phenylacetic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With glucose-diphenylaminium tosylate-derived carbon solid acid (GDTCSA) In n-heptane at 80℃; for 1h;99%
With monoammonium 12-tungstophosphate for 12h; Heating;98%
With [bis(acetoxy)iodo]benzene; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 16h; Mitsunobu reaction;97%
benzyl alcohol
100-51-6

benzyl alcohol

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With C16H25N3O2S In n-heptane for 48h; Reflux; Molecular sieve; Inert atmosphere;99%
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 4-pyrrolidin-1-ylpyridine In octane for 6h; Reflux;98%
With SO3H and NH2+ functional carbon-based solid acid at 80℃; for 6h;92%
benzyl 2-hydroxy-2-phenylacetate
62173-99-3, 80409-16-1, 97415-09-3, 890-98-2

benzyl 2-hydroxy-2-phenylacetate

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
Stage #1: benzyl 2-hydroxy-2-phenylacetate With dmap; triethylamine; chlorophosphoric acid diphenyl ester In tetrahydrofuran at 20℃;
Stage #2: With dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran; 1,2-dimethoxyethane at 75℃;
99%
2,6-dimethylpyridine
108-48-5

2,6-dimethylpyridine

phenylacetic acid
103-82-2

phenylacetic acid

2-chloro-1-methyl-pyridinium iodide
14338-32-0

2-chloro-1-methyl-pyridinium iodide

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With benzyl alcohol In dichloromethane98%
phenylacetic acid
103-82-2

phenylacetic acid

2-chloro-1-methyl-pyridinium iodide
14338-32-0

2-chloro-1-methyl-pyridinium iodide

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With tributyl-amine; benzyl alcohol In diethyl ether97%
phenylacetic acid
103-82-2

phenylacetic acid

2-bromo-1-methyl-pyridinium iodide
52693-56-8

2-bromo-1-methyl-pyridinium iodide

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With tributyl-amine; benzyl alcohol In dichloromethane97%
3-(2-phenylacetyl)-1,3-oxazolidin-2-one
109853-53-4

3-(2-phenylacetyl)-1,3-oxazolidin-2-one

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
lanthanum(III) iodide In tetrahydrofuran Ambient temperature;95%
phenylacetic acid
103-82-2

phenylacetic acid

1-ethyl-2-iodoquinolinium iodide
4800-58-2

1-ethyl-2-iodoquinolinium iodide

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With tributyl-amine; benzyl alcohol In dichloromethane95%
phenylacetic acid
103-82-2

phenylacetic acid

2-chloro-1-ethyl-4-methoxypryridinium tetrafluoroborate

2-chloro-1-ethyl-4-methoxypryridinium tetrafluoroborate

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With triethylamine; benzyl alcohol In dichloromethane95%
phenylacetic acid
103-82-2

phenylacetic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 0℃; for 1h;94%
With dmap; triethylamine 1.) CH2Cl2, 0 deg C, 5 min, 2.) 0 deg C, 1 h; Yield given. Multistep reaction;
(S)-4-iso-propyl-3-(2'-phenylacetyl)oxazolidin-2-one
103422-95-3, 138690-03-6

(S)-4-iso-propyl-3-(2'-phenylacetyl)oxazolidin-2-one

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
lanthanum(III) iodide In tetrahydrofuran Ambient temperature;93%
carbon monoxide
201230-82-2

carbon monoxide

benzyl alcohol
100-51-6

benzyl alcohol

A

phenylacetic acid
103-82-2

phenylacetic acid

B

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

C

toluene
108-88-3

toluene

Conditions
ConditionsYield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 44h; Carbonylation; reduction;A 90%
B 3%
C 6%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 44h;A 90 % Spectr.
B 3 % Spectr.
C 6 % Spectr.
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 44h;A 24 % Spectr.
B 58 % Spectr.
C 7 % Spectr.
phenylacetic acid
103-82-2

phenylacetic acid

benzylamine
100-46-9

benzylamine

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With sodium nitrite In acetonitrile at 0 - 20℃; for 0.416667h;90%
2-iodobenzyl 2-chloro-2-phenylacetate
1166870-60-5

2-iodobenzyl 2-chloro-2-phenylacetate

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With [Ir(2-phenylpyridine)-2-(4,4’-di-tert-butyl-2,2’-bipyridine)]PF6; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1h; Irradiation;90%
With [Ir(2-phenylpyridine)-2-(4,4’-di-tert-butyl-2,2’-bipyridine)]PF6; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 3h; Irradiation;
Benzeneacetamide
103-81-1

Benzeneacetamide

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In n-heptane at 100℃; for 24h;90%
With cerium(IV) oxide In 1,3,5-trimethyl-benzene at 165℃; for 22h; Inert atmosphere;86%
phenylacetyl fluoride
370-84-3

phenylacetyl fluoride

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;88%
p-toluidine
106-49-0

p-toluidine

(2RS)-2-benzyloxy-3-phenylpropanal
256229-10-4

(2RS)-2-benzyloxy-3-phenylpropanal

A

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

B

N-(4-methylphenyl)formamide
3085-54-9

N-(4-methylphenyl)formamide

Conditions
ConditionsYield
With trifluoroacetic acid In toluene at 50℃; for 1h;A 86%
B n/a
Ethyl 2-phenylethanoate
101-97-3

Ethyl 2-phenylethanoate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With titanium(IV) tetraethanolate at 110℃; for 15h;85%
bromobenzene
108-86-1

bromobenzene

benzyl glycolate
30379-58-9

benzyl glycolate

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide; nickel dibromide In 1-methyl-pyrrolidin-2-one at 20℃; for 14h; Glovebox; Electrolysis;85%
Phenyl-acetic acid [2,2']bipyridinyl-6-yl ester
75178-11-9

Phenyl-acetic acid [2,2']bipyridinyl-6-yl ester

benzyl alcohol
100-51-6

benzyl alcohol

A

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

B

<2,2'-bipyridin>-6(1H)-one
101001-90-5

<2,2'-bipyridin>-6(1H)-one

Conditions
ConditionsYield
With cesium fluoride In dichloromethane for 72h; Ambient temperature;A 83%
B n/a
phenylacetic acid
103-82-2

phenylacetic acid

A

7β-[α-carboxy-α-phenylacetamido]-3-methyl-Δ3 -0-2-isocephem-4-carboxylic acid

7β-[α-carboxy-α-phenylacetamido]-3-methyl-Δ3 -0-2-isocephem-4-carboxylic acid

B

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; benzyl alcohol In tolueneA n/a
B 83%
N,N,N-­trimethyl-­1-­phenylmethanaminium trifluoromethanesulfonate
260783-80-0

N,N,N-­trimethyl-­1-­phenylmethanaminium trifluoromethanesulfonate

carbon monoxide
201230-82-2

carbon monoxide

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine In toluene at 100℃; under 760.051 Torr; for 12h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Schlenk technique;82%
phenylacetic acid
103-82-2

phenylacetic acid

benzyl chloride
100-44-7

benzyl chloride

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate; potassium iodide In diethoxymethane at 80 - 85℃; for 6h;81%
With triethylamine at 90℃; for 2h;70%
With potassium fluoride; 1,3-dimethylimidazolinium methanesulfonate at 90℃; for 2h;
(S)-4-benzyl-3-phenylacetyl-2-oxazolidinone
104266-89-9

(S)-4-benzyl-3-phenylacetyl-2-oxazolidinone

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
lanthanum(III) iodide In tetrahydrofuran Ambient temperature;78%
3,3,6,6-tetrabenzyl-1,2,4,5-tetraoxan
71916-06-8

3,3,6,6-tetrabenzyl-1,2,4,5-tetraoxan

A

phenylacetic acid
103-82-2

phenylacetic acid

B

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

C

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

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

D

1,3-Diphenylpropanone
102-04-5

1,3-Diphenylpropanone

Conditions
ConditionsYield
In benzene at 150℃; for 72h; Product distribution; Mechanism; thermolysis; var. temp., time and solvent;A n/a
B 12%
C 77%
D 2%
carbon monoxide
201230-82-2

carbon monoxide

benzyl bromide
100-39-0

benzyl bromide

A

phenylacetic acid
103-82-2

phenylacetic acid

B

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

C

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

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

D

toluene
108-88-3

toluene

E

1,3-Diphenylpropanone
102-04-5

1,3-Diphenylpropanone

Conditions
ConditionsYield
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; benzene at 20℃; under 760 Torr; for 15h; Product distribution; variation of solvent, temperature, catalyst, pressure, reaction time and ratio of catalyst and substrate, examinations with further benzyl halides;A 75%
B 3%
C 6%
D 2%
E 14%
carbon monoxide
201230-82-2

carbon monoxide

benzyl trifluoroacetate
351-70-2

benzyl trifluoroacetate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; triethylamine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 100℃; for 24h;74%
methanol
67-56-1

methanol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Conditions
ConditionsYield
With tert-butylamine; lithium bromide for 0.25h; Heating;100%
With indium; iodine for 12h; transesterification; Heating;88%
In acetonitrile Ambient temperature; Et4NClO4 electrolyte, glassy carbon cathode, Pt anode, -1,7 V potential;43%
With PCS-DBU In water at 60℃; Rate constant; Mechanism; other quaternary ammonium resins, other temperatures, other reaction time;
benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

phenylacetic acid
103-82-2

phenylacetic acid

Conditions
ConditionsYield
With scandium(III) tris(trifluoromethylsulfonyl)methide; methoxybenzene at 100℃; for 0.5h; debenzylation;100%
Stage #1: benzyl 2-phenylacetate With sodium methylate; dimethylsulfoxonium methylide In tetrahydrofuran at 20℃; for 0.666667h;
Stage #2: With hydrogenchloride; water In ethyl acetate
90%
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.166667h; chemoselective reaction;83%
benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

2-phenylethanol
60-12-8

2-phenylethanol

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; hafnium tetrachloride In tetrahydrofuran at -20℃; for 3h; Inert atmosphere;99%
With (Ppyz)Zr(BH4)2Cl2 In diethyl ether for 8h; Heating;92%
With phenylsilane; potassium tert-butylate; water; sodium triethylborohydride; cobalt(II) chloride In 1,4-dioxane; toluene at 60℃; for 15h; Inert atmosphere; Glovebox; Schlenk technique;84%
carbon monoxide
201230-82-2

carbon monoxide

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

A

phenylacetic acid
103-82-2

phenylacetic acid

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 100℃; under 76000 Torr; for 42h; Carbonylation; reduction;A 98%
B 17%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

(1-(benzyloxy)-2-phenylethoxy)trimethylsilane

(1-(benzyloxy)-2-phenylethoxy)trimethylsilane

Conditions
ConditionsYield
Stage #1: benzyl 2-phenylacetate With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h; Inert atmosphere;
Stage #2: trimethylsilyl trifluoromethanesulfonate With pyridine In dichloromethane at -78℃; for 3h; Inert atmosphere;
Stage #3: With sodium tartrate; potassium tartrate In dichloromethane; water at -78℃; for 0.25h; Inert atmosphere;
91%
benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

diphenyl diselenide
1666-13-3

diphenyl diselenide

A

phenylacetic acid
103-82-2

phenylacetic acid

B

benzyl phenyl selenide
18255-05-5

benzyl phenyl selenide

Conditions
ConditionsYield
Stage #1: diphenyl diselenide With aluminum (III) chloride; zinc In acetonitrile at 70℃; under 760.051 Torr; for 1.25h; Neutral;
Stage #2: benzyl 2-phenylacetate In acetonitrile at 70℃; under 760.051 Torr; for 12h; Neutral;
A 88%
B n/a
benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

benzoyl chloride
98-88-4

benzoyl chloride

3-oxo-2,3-diphenylpropionic acid benzyl ester
512176-69-1

3-oxo-2,3-diphenylpropionic acid benzyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;87%
benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

α-diazo-α-phenylacetic acid benzyl ester
218792-82-6

α-diazo-α-phenylacetic acid benzyl ester

Conditions
ConditionsYield
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;86%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;86%
Stage #1: benzyl 2-phenylacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.416667h;
Stage #2: With 4-acetamidobenzenesulfonyl azide In acetonitrile
80%
benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

benzyl 2-azido-2-phenylacetate
1263368-81-5

benzyl 2-azido-2-phenylacetate

Conditions
ConditionsYield
With sodium azide; 4,4'-bis-(dichloroiodo)-biphenyl; triethylamine In 1,4-dioxane for 4h; Reflux;85%
Multi-step reaction with 2 steps
1: 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere; Schlenk technique
2: tris(pentafluorophenyl)borate; trimethylsilylazide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique; Molecular sieve
View Scheme

102-16-9Relevant articles and documents

Preparation of acyl fluorides with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide

Chen, Chinpiao,Chien, Chin-Tzu,Su, Chu-Hsiang

, p. 75 - 77 (2002)

This work presents an efficient procedure for preparing acyl fluorides by simply reacting carboxylic acid with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide (DCC) in dichloromethane. The acyl fluorides were converted in situ to the corresponding benzyl carboxylic esters by adding benzyl alcohol and triethylamine to the reaction mixture.

Efficient esterification of carboxylic acids with alkyl halides catalyzed by fluoride ions in ionic liquids

Brinchi,Germani,Savelli

, p. 6583 - 6585 (2003)

Ionic liquids based on 1,3-dialkylimidazolinium methanesulfonate have been used as efficient reusable reaction media in the esterification of several carboxylic acids with alkyl halides catalyzed by fluoride ions. The method has wide applicability, and it is mild and green; it is useful for the protection of acids, via ester formation, for alkali labile molecules.

S,S-Bis Dithiocarbonate. A New Reactive Coupling Agent for the Direct Esterification of Carboxylic Acids

Kim, Sunggak,Kim, Sung Soo

, p. 1017 - 1019 (1986)

S,S-Bis dithiocarbonate, prepared from 4,6-dimethyl-2-pyrimidinethiol hydrochloride and phosgene in the presence of triethylamine in dichloromethane/toluene, is a new reactive coupling agent for the direct esterification of carboxylic acids with alcohols.

Use of diethoxymethane as a solvent for phase-transfer esterification of carboxylic acids

Coleman, M. Todd

, p. 1911 - 1913 (2012)

The esterification of carboxylic acids with selected primary alkyl halides in diethoxymethane (DEM) utilizing solid-liquid phase-transfer catalysis has been studied. The use of DEM as the solvent simplifies the process in that a single solvent can be used for both reaction and workup.

-

Williams,K.,Halpern,B.

, p. 727 - 728 (1974)

-

One-electron Oxidation of Carboxylates by Hexachloroosmate(V) Ion

Eberson, Lennart,Nilsson, Monica

, p. 1041 - 1042 (1992)

Hexachloroosmate(V) cleanly oxidizes tetrabutylammonium tert-butylcyanoacetate to decarboxylative-coupling products, meso- and rac-2,3-di-tert-butylsuccinonitrile, thus constituting the first metal ion-based oxidant to be found to simulate properly this aspect of the Kolbe anodic oxidation of carboxylates.

-

Inomata et al.

, p. 1866 (1978)

-

Mercury(II) Oxide/Tetrafluoroboric Acid; A General Method for Esters from Carboxylic Acids and Alkyl Halides

Barluenga, Jose,Alonso-Cires, Luisa,Campos, Pedro, J.,Asensio, Gregorio

, p. 649 - 651 (1983)

-

Palladium-catalyzed carbonylation of benzyl alcohol and its analogs promoted by HI in aqueous systems

Lin, Yong-Shou,Yamamoto, Akio

, p. 3747 - 3750 (1997)

Carbonylation of benzyl alcohol catalyzed by a palladium(0) complex and promoted by hydrogen iodide gives phenylacetic acid in excellent yields in aqueous systems. The catalysis is proposed to proceed through a benzylpalladium species formed by the oxidative addition of benzyl iodide, produced in situ by the interaction of benzyl alcohol with HI, to a Pd(0) species. Application of the carbonylation process to other arylmethanol analogs provided convenient means to prepare 3-isochromanone, 1,4-benzenediacetic acid, 2-hydroxybenzeneacetic acid and 2-naphthaleneacetic acid.

Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides

Li, Zijian,Sun, Wenxuan,Wang, Xianxu,Li, Luyang,Zhang, Yong,Li, Chao

supporting information, p. 3536 - 3543 (2021/03/08)

As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil

supporting information, p. 6709 - 6713 (2021/09/08)

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

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