Synthesis of ethyl cinnamate

Preparation of ethyl cinnamate

Preparation of ethyl cinnamate

Preparation of ethyl cinnamate

To 50 g of ethyl acetate are added 23 g of sodium in the form of wire. The flask is cooled in ice, and, with slight shaking, 10 g of benzaldehyde are gradually added. When all the sodium has gone into solution, the flask is set aside for 2 hours, when it is acidified with dilute acetic acid. The ethyl cinnamate layer which separates is removed, shaken up with dilute sodium carbonate solution, and dried over calcium chloride. It is then distilled, the fraction 265-275 ° being retained. The yield of ethyl cinnamate is 65%; colorless liquid; insoluble in water; b.p. 271° C.

Systematic organic chemistry, by W. M. Cumming, 143, 1937.

IUPAC Name

ethyl (E)-3-phenylprop-2-enoate

InChI

InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+

InChI Key

KBEBGUQPQBELIU-CMDGGOBGSA-N

Canonical SMILES

CCOC(=O)C=CC1=CC=CC=C1

Isomeric SMILES

CCOC(=O)/C=C/C1=CC=CC=C1

MeSH Synonyms

ethyl cinnamate

Depositor-Supplied Synonyms

ETHYL CINNAMATE, 103-36-6, Cinnamic acid ethyl ester, Ethyl 3-phenylacrylate, Cinnamic acid, ethyl ester, Ethylcinnamoate, Ethyl trans-cinnamate, (E)-ethyl cinnamate, 2-Propenoic acid, 3-phenyl-, ethyl ester, Ethyl benzylideneacetate, ethyl (E)-3-phenylprop-2-enoate, Ethyl 3-phenylpropenoate, Ethyl beta-phenylacrylate, ethyl (2E)-3-phenylprop-2-enoate, Ethyl cinnamate (natural), UNII-C023P3M5JJ, Ethylcinnamate, Ethyl 3-phenyl-2-propenoate, FEMA No. 2430, CHEBI:4895, CHEMBL318196, KBEBGUQPQBELIU-CMDGGOBGSA-N, NSC 6773, EINECS 203-104-6, SBB060754, BRN 1238804, 3-Phenyl-2-propenoic acid, ethyl ester, AI3-00667, 2-Propenoic acid, 3-phenyl-, ethyl ester, (E)-, T6872234, Ethyl Cinnamate Trans, Ethyl 3-phenylprop-2-enoate, InChI=1/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8, trans-Ethyl cinnamate, Ethyl (E)-cinnamate, AC1LCUWH, Ethyl cinnamate, trans, Benzeneacrylic acid ethyl, 3-Phenylpropenoic acid ethyl, Ethyl trans-3-Phenylacrylate, WLN: 2OV1U1R, BIDD:ER0267, ethyl (2E)-3-phenylacrylate, SCHEMBL112445, W243000_ALDRICH, W243019_ALDRICH, 112372_ALDRICH, AC1Q647X, C023P3M5JJ, trans-cinnamic acid ethyl ester, CINNAMIC ACID,ETHYL ESTER, NSC6773, MolPort-001-779-802, MolPort-009-209-092, 3-Phenyl-acrylic acid, ethyl ester, NSC-6773, Ethyl (2E)-3-phenyl-2-propenoate, AR-1I8920, ZINC12358720, AKOS008947908, Ethyl (2E)-3-phenyl-2-propenoate #, LS-2716, RTR-030843, trans-3-Phenylacrylic Acid Ethyl Ester, (E)-3-Phenyl-acrylic acid ethyl ester, AJ-61316, AK150804, AN-24632, CJ-13818, OR025188, OR195578, TR-030843, FT-0623830, FT-0668209, FT-0693346, ST24047165, ST50826879, C06359, I01-7775, 3B3-026920, 403649-38-7

Removed Synonyms

2-Propenoic acid, ethyl ester, c0359, CID637758, H143, C451418, 4192-77-2, 10389-63-6

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