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103-41-3

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103-41-3 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 103-41-3 differently. You can refer to the following data:
1. Clear colorless to yellowish crystalline mass or liquid after meltin
2. Benzyl Cinnamate occurs in balsams and balsam oils. It forms white, sweet-balsamic-smelling crystals (mp 35-36°C). Benzyl cinnamate is used as a fixative in perfumes and as a component of heavy, oriental perfumes.
3. Benzyl cinnamate has a sweet, balsamic odor and a honey-like taste.

Occurrence

Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam.

Uses

Different sources of media describe the Uses of 103-41-3 differently. You can refer to the following data:
1. In artificial flavors, in perfumes, mainly as a fixative.
2. Benzyl cinnamate has been employed as internal standard during the determination of compounds commonly added to personal care products such as UV filters and antimicrobial agents in environmental samples.

Preparation

By heating benzyl chloride and excess sodium cinnamate in water to 100 to 115°C; by heating sodium cinnamate with an excess of benzyl chloride in the presence of diethylamine.

Production Methods

Benzyl cinnamate is produced by the direct esterification of benzyl alcohol with cinnamic acid.

Taste threshold values

Taste characteristics at 50 ppm: spicy, floral, fruity, balsamic.

General Description

Benzyl cinnamate is widely used as a fragrance ingredient.

Hazard

Moderately toxic.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. Amild allergen and skin irritant. Combustible liquid. When heated to decomposition it emits acridsmoke and irritating fumes.

Metabolism

See monograph on Benzyl alcohol (p. 1011).

Purification Methods

Recrystallise the ester to a constant melting point from 95% EtOH. It has the odour of balsam. Alternatively dissolve it in Et2O, wash it with 10% aqueous Na2CO3, H2O, dry (Na2SO4), evaporate and fractionate it under reduced pressure using a short Vigreux column (p 11). It decomposes when boiled at atmospheric pressure. [Eliel & Anderson J Am Chem Soc 74 547 1952, Bender & Zerner J Am Chem Soc 84 2550 1962, Beilstein 9 IV 2012.]

Check Digit Verification of cas no

The CAS Registry Mumber 103-41-3 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 3 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 103-41:
(5*1)+(4*0)+(3*3)+(2*4)+(1*1)=23
23 % 10 = 3
So 103-41-3 is a valid CAS Registry Number.
InChI:InChI=1/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2

103-41-3 Well-known Company Product Price

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  • TCI America

  • (C0358)  Benzyl Cinnamate  >98.0%(GC)

  • 103-41-3

  • 25g

  • 160.00CNY

  • Detail
  • TCI America

  • (C0358)  Benzyl Cinnamate  >98.0%(GC)

  • 103-41-3

  • 500g

  • 1,240.00CNY

  • Detail
  • Alfa Aesar

  • (A19550)  Benzyl cinnamate, 99%   

  • 103-41-3

  • 100g

  • 387.0CNY

  • Detail
  • Alfa Aesar

  • (A19550)  Benzyl cinnamate, 99%   

  • 103-41-3

  • 500g

  • 1477.0CNY

  • Detail
  • Sigma-Aldrich

  • (69139)  Benzylcinnamate  analytical reference material

  • 103-41-3

  • 69139-100MG

  • 749.97CNY

  • Detail

103-41-3SDS

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 Benzyl cinnamate

1.2 Other means of identification

Product number -
Other names Benzyl ciamate

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:103-41-3 SDS

103-41-3Synthetic route

Benzyl acetate
140-11-4

Benzyl acetate

benzaldehyde
100-52-7

benzaldehyde

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; Inert atmosphere; stereoselective reaction;99%
With iodine; magnesium; mercury dichloride Reagens 4: Xylol;
trans-cinnamoyl fluoride
38986-89-9

trans-cinnamoyl fluoride

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;99%
sodium phenyl-methanolate
20194-18-7

sodium phenyl-methanolate

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;98%
iodobenzene
591-50-4

iodobenzene

benzylacrylate
2495-35-4

benzylacrylate

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With C40H42N6O4Pd(2+)*2Br(1-); potassium carbonate In water at 80℃; for 4h; Reagent/catalyst; Heck Reaction;98%
With potassium carbonate; di(μ-acetato)-bis(7-fluoro-2,4,8-trimethylquinoline)Pd2 In N,N-dimethyl-formamide at 140℃; Heck reaction;
(E)-benzyl-3-(2-((E)-piperidin-1-yldiazenyl)phenyl)acrylate
1399175-32-6

(E)-benzyl-3-(2-((E)-piperidin-1-yldiazenyl)phenyl)acrylate

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere;98%
Methyl cinnamate
103-26-4

Methyl cinnamate

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve In tetrahydrofuran at 20℃; for 3h;97%
1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 3h;97%
With iron(III)-acetylacetonate In n-heptane at 105℃; for 10h; Inert atmosphere;96%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

benzyl bromide
100-39-0

benzyl bromide

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.75h; Esterification;97%
Stage #1: (E)-3-phenylacrylic acid With caesium carbonate In methanol; water at 0℃; pH=7;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;
96%
With potassium carbonate In acetonitrile for 8h; Reflux;94%
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 6h;85%
malonic acid monobenzyl ester
40204-26-0

malonic acid monobenzyl ester

benzaldehyde
100-52-7

benzaldehyde

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With piperidine; dmap In N,N-dimethyl-formamide at 25℃; Doebner-Knoevenagel reaction;96%
With dmap In N,N-dimethyl-formamide at 25℃; Knoevenagel reaction;96%
O-benzyl-N-cyclohexyl-N\-methylpolystyrene isourea

O-benzyl-N-cyclohexyl-N\-methylpolystyrene isourea

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
In acetonitrile at 125℃; for 0.05h; microwave irradiation;96%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

benzaldehyde
100-52-7

benzaldehyde

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
dmap In N,N-dimethyl-formamide at 20℃; for 5h;96%
C24H19NO3

C24H19NO3

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With trimethylphosphane In dichloromethane; toluene at 20℃; for 3h;96%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With TiO(acac)2 In xylene for 12h; Heating;95%
With 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1,-dioxide; triethylamine In dichloromethane -10 deg C -> r.t., overnight;92%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 10h; Heating;92%
sodium trans-cinnamate
18509-03-0

sodium trans-cinnamate

benzyl chloride
100-44-7

benzyl chloride

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 1,3-dimethylimidazolinium methanesulfonate at 90℃; for 0.5h;95%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: benzyl alcohol With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide; benzylamine In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: (E)-3-phenylpropenal With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
95%
With 4-methyl-3-(2,4,6-trimethylphenyl)thiazolium tetrafluoroborate; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 7h; Inert atmosphere; Electrochemical reaction;83%
Stage #1: benzyl alcohol With 1,3-bis(2-(2-methoxyethyl)-6-methylphenyl)-1H-imidazol-3-ium perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: (E)-3-phenylpropenal With 1,1'-bis(4-oxo-3,5-di-t-butylcyclohexa)dienylidene In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Inert atmosphere;
77 %Spectr.
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

2-(phenylmethoxy)benzaldehyde
5896-17-3

2-(phenylmethoxy)benzaldehyde

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;95%
3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one
109299-93-6

3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With [t-Bu2SnCl(OH)]2 In toluene for 14h; Heating;94%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

2'-benzyloxyacetophenone
31165-67-0

2'-benzyloxyacetophenone

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Inert atmosphere; Schlenk technique;94%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

1,2-di(benzyloxy)benzene
10403-73-3

1,2-di(benzyloxy)benzene

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Inert atmosphere; Schlenk technique;93%
benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
zinc(II) chloride In dichloromethane; acetonitrile for 18h; Ambient temperature;92%
Benzyl acetate
140-11-4

Benzyl acetate

Methyl cinnamate
103-26-4

Methyl cinnamate

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With sodium 4-tert-butylphenolate; sodium t-butanolate In tetrahydrofuran92%
2-benzyloxy-1-methylpyridinium triflate

2-benzyloxy-1-methylpyridinium triflate

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With triethylamine In various solvent(s) at 83℃; for 24h;92%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

2,4,6-tris(benzyloxy)-1,3,5-triazine
7285-83-8

2,4,6-tris(benzyloxy)-1,3,5-triazine

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5.5h; Molecular sieve;91%
benzylacrylate
2495-35-4

benzylacrylate

C17H12F5NO2

C17H12F5NO2

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With tetrakis(acetonitrile)palladium bistriflate; (S)-4-methyl-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole; sodium carbonate; silver carbonate In 1,2-dichloro-ethane at 130℃; for 12h; Heck Reaction; Sealed tube; Inert atmosphere;91%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

N,N'-diisopropyl-O-benzyl isourea
2978-10-1, 113282-06-7

N,N'-diisopropyl-O-benzyl isourea

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 130℃; for 0.0833333h; Irradiation;90%
iron pentacarbonyl
13463-40-6, 71564-23-3

iron pentacarbonyl

phenylacetylene
536-74-3

phenylacetylene

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 0.5h; regioselective reaction;90%
Cinnamic acid
621-82-9

Cinnamic acid

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 22h; Esterification;89%
With triethylamine In dichloromethane 1.) 0 deg C; 2.) to room temperature and 1 h;87%
α-chloro-cinnamaldehyde
18365-42-9

α-chloro-cinnamaldehyde

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20℃; Inert atmosphere; optical yield given as %de; stereoselective reaction;88%
bromobenzene
108-86-1

bromobenzene

benzylacrylate
2495-35-4

benzylacrylate

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With C40H42N6O4Pd(2+)*2Br(1-); potassium carbonate In water at 80℃; for 5.5h; Heck Reaction;86%
With potassium carbonate In ethanol; water at 80℃; for 2h; Catalytic behavior; Heck Reaction;
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazine

2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazine

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 0.0166667h; Molecular sieve; Inert atmosphere;86%
Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;84%
(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

Benzyl 3-phenylpropionate
22767-96-0

Benzyl 3-phenylpropionate

Conditions
ConditionsYield
With hydrogen In toluene at 25℃; for 1h; Catalytic behavior;99%
With hydrogen; palladium In tetrahydrofuran for 24h;98%
With hydrogen; TMSB; palladium In ethanol at 20℃; under 760 Torr; for 24h;98%
(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;97%
With ammonium formate; silica gel; palladium dichloride In formic acid; water for 0.133333h; microwave irradiation;84%
(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

Conditions
ConditionsYield
With phosphate buffer; Bacillus sublilis esterase In methanol; hexane at 37℃; for 24h; Product distribution; Further Variations:; Reagents;95%
(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

phenylboronic acid
98-80-6

phenylboronic acid

(S,R)-4-(benzyloxycarbonyl)-2,5-diphenyl-1,3,2-dioxaborolane

(S,R)-4-(benzyloxycarbonyl)-2,5-diphenyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With K2; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium carbonate In tert-butyl alcohol at 20℃; for 12h;95%
(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

(2,4,6-trimethoxyphenyl)methanethiol
212555-23-2

(2,4,6-trimethoxyphenyl)methanethiol

C26H28O5S

C26H28O5S

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Michael addition;91%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

DL-benzyl (1R,2R)-2,3,3-triphenylcyclobutane-1-carboxylate

DL-benzyl (1R,2R)-2,3,3-triphenylcyclobutane-1-carboxylate

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In dichloromethane at 20℃; for 5h; Inert atmosphere; Sealed tube; Irradiation; diastereoselective reaction;91%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

(E)-cinnamic acid benzyl ester
103-41-3

(E)-cinnamic acid benzyl ester

benzyl 2,3,3-triphenylcyclobutyl-1-carboxylate

benzyl 2,3,3-triphenylcyclobutyl-1-carboxylate

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III) In 1,2-dichloro-ethane at 25℃; for 5h; Inert atmosphere; Irradiation;91%

103-41-3Relevant articles and documents

Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate

Tummatorn, Jumreang,Albiniak, Philip A.,Dudley, Gregory B.

, p. 8962 - 8964 (2007)

(Chemical Equation Presented) Triethylamine (Et3N) mediates esterification reactions between the title reagent (1) and carboxylic acids. Alcohols, phenols, amides, and other sensitive functionality are not affected; a dual role for Et3N as a promoter and a scavenger is postulated. Benzyl esters are obtained from substrates including amino acid and sugar derivatives.

METAL-CATALYZED SYNTHESIS OF CARBOXYLIC ESTERS UTILIZING (E)-PHENYL 2-PYRIDYL KETONE O-ACYLOXIMES (PPAO)

Miyasaka, Tadayo,Ishizu, Hidehiro,Sawada, Akihiro,Fujimoto, Akiko,Noguchi, Shunsaku

, p. 871 - 874 (1986)

(E)-Phenyl 2-pyridyl ketone O-acyloximes (PPAO) could be highly activated by metal ions such as Fe(3+), Cu(2+), and Zn(2+), and the most effective catalyst for the synthesis of carboxylic esters was found to be Zn(2+).Furthermore, sterically hindered carboxylic esters were easily obtained utilizing PPAOs and alcoholates in high yields.

A simple one-pot organometallic formylation/trapping sequence using N-formylcarbazole

Dixon, Darren J.,Lucas, Amanda C.

, p. 1092 - 1094 (2004)

Treatment of a range of sp3-, sp2- and sp-nucleophiles with N-formyl carbazole leads to the formation of the metastable anionic carbazole carbinols. In the presence of a second nucleophilic reagent such as phosphonoacetate or an organolithium, these collapse on warming to the aldehyde which is trapped in situ to afford the α,β-unsaturated esters or secondary carbinols respectively.

Protonation of homoenolate equivalents generated by N-heterocyclic carbenes

Maki, Brooks E.,Chan, Audrey,Scheidt, Karl A.

, p. 1306 - 1315 (2008)

Homoenolate equivalents are generated by Lewis basic N-heterocyclic carbene catalysts and then protonated to generate efficiently saturated esters from unsaturated aldehydes. This reactivity is extended to the generation of β-acylvinyl anions from alkynyl aldehydes. The asymmetric protonation of a homoenolate equivalent generated from a β,β-disubstituted aldehyde can be accomplished with a chiral N-heterocyclic carbene. Georg Thieme Verlag Stuttgart.

N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

Grasa, Gabriela A.,Kissling, Rebecca M.,Nolan, Steven P.

, p. 3583 - 3586 (2002)

(graph presented) Imidazol-2-ylidenes, a family of N-heterocyclic carbones (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl-or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.

N-Methylpyrrolidin-2-one-Promoted Formation of Functional Esters through C–O Bond Cleavage

Liu, Jianming,Wang, Yanyan,Yue, Yuanyuan,Liu, Na,Zhang, Jian,Zhao, Shufang,Tang, Qinghu,Zhuo, Kelei

, p. 2641 - 2647 (2017)

Trifluoromethanesulfonic acid catalyzed C–O bond cleavage leading to the preparation of functional esters in the presence of N-methylpyrrolidin-2-one (NMP) was accomplished. Various substrates were well tolerated, and a gram-scale experiment was successfully realized. DFT calculations indicated that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the functional esters in chlorobenzene.

Development and Applications of Transesterification Reactions Catalyzed by N-Heterocyclic Olefins

Blümel, Marcus,Noy, Janina-Miriam,Enders, Dieter,Stenzel, Martina H.,Nguyen, Thanh V.

, p. 2208 - 2211 (2016)

A novel method to utilize N-heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocycic carbenes, as organocatalysts to promote transesterification reactions has been developed. Because of their strong Br?nsted/Lewis basicity, NHOs can enhance the nucleophilicity of alcohols for their acylation reactions with carboxylic esters. This transformation can be employed in industrially relevant processes such as the production of biodiesel, the depolymerization of polyethylene terephthalate (PET) from plastic bottles for recycling purposes, and the ring-opening polymerization of cyclic esters to form biodegradable polymers such as polylactide (PLA) and polycaprolactone (PCL).

Synthetic Methods and Reactions; 97. Sulfuryl Chloride Fluoride-Mediated Esterification of Carboxylic Acids with Alcohols

Olah, George A.,Narang, Subhash C.,Garcia-Luna, Armando

, p. 790 - 791 (1981)

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An Exceedingly Efficient and Chemoselective Esterification with Activated Alcohols Using AlCl3/NaI/CH3CN System

Karade,Shirodkar,Potrekar,Karade

, p. 391 - 396 (2004)

A combination of hard Lewis acid AlCl3 and a soft nucleophile NaI in acetonitrile has been used as an efficient system for the selective esterification reaction between aromatic carboxylic acid and alcohol.

Acaricidal activity of tonka bean extracts. Synthesis and structure-activity relationships of bioactive derivatives

Gleye, Christophe,Lewin, Guy,Laurens, Alain,Jullian, Jean-Christophe,Loiseau, Philippe,Bories, Christian,Hocquemiller, Reynald

, p. 690 - 692 (2003)

The acaricidal effects of tonka bean, Dipterix odorata, extracts were investigated on Dermatophagoides pteronyssinus, the European house dust mite, and compared with benzyl benzoate as a standard acaricidal compound. A cyclohexane extract was the most effective, with an EC50 = 0.075 g/m2 after a 24 h period, as compared with benzyl benzoate (0.025 g/m2). Bioassay-guided fractionation of this extract led to the isolation of coumarin (1). Pharmacomodulation of this compound led us to test 20 analogues (2-21), which were either synthesized or purchased.

Water-tolerant and reusable catalysts for direct ester condensation between equimolar amounts of carboxylic acids and alcohols

Nakayama, Masaya,Sato, Atsushi,Ishihara, Kazuaki,Yamamoto, Hisashi

, p. 1275 - 1279 (2004)

ZrOCl2 · 8 H2O and HfOCl2 · 8 H2O are highly effective, water-tolerant, and reusable homogeneous catalysts for direct ester condensation be-tween equimolar amounts of carboxylic acids and alcohols. Notably, zirconium(IV) salts such as ZrOCl2 · 8 H2O and Zr(OAc)x(OH)y are potential green catalysts due to their low toxicity, commercial availability at low cost, ease of handling, high catalytic activity, and reusability.

Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents

Moayyed, Mohammadesmaeil,Saberi, Dariush

, p. 445 - 455 (2021)

Abstract: Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80?°C. DES/TBAI system was reused up to five consecutive times. Graphic abstract: Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.[Figure not available: see fulltext.].

Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E, E)-1,3-Dienes

Dethe, Dattatraya H.,Beeralingappa, Nagabhushana C.,Uike, Amar

, p. 3444 - 3455 (2021/02/16)

An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst.

Benzyne-Mediated Esterification Reaction

Li, Yang,Shi, Jiarong,Zhao, Jinlong

supporting information, p. 7274 - 7278 (2021/10/01)

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

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