Synthesis of cinnamic acid

Preparation of cinnamic acid

Preparation of cinnamic acid

Preparation of cinnamic acid

A mixture of 20 grams of benzaldehyde, 30 grams of acetic anhydride, both freshly distilled, and 10 grams of anhydrous pulverized sodium acetate, is heated in a flask fitted with a reflux condenser, for 8 hours, at 180° C. After the reaction is complete, the hot reaction product is poured into a large flask. Water is added and then distilled with steam, until no more benzaldehyde passes over. The quantity of water used here is large enough so that all of the cinnamic acid dissolves except a small portion of an oily impurity. The solution is then boiled a short time, with some activated charcoal, and filtered. On cooling, the cinnamic acid separates out in lustrous leaves. Purification is performed by crystallization from water. Reaction yield is about 15 grams and the melting point of pure cinnamic acid – 133° C.

Practical organic chemistry. 1956, 713-714.

IUPAC Name

(E)-3-phenylprop-2-enoic acid

InChI

InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

InChI Key

WBYWAXJHAXSJNI-VOTSOKGWSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CC(=O)O

Isomeric SMILES

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

MeSH Synonyms

cinnamic acid, cinnamic acid, (trans)-(E)-isomer, cinnamic acid, (Z)-isomer, cinnamic acid, 13C-labeled cpd, cinnamic acid, 14C-labeled cpd, cinnamic acid, 14C-labeled cpd (E)-isomer, cinnamic acid, 2-(13)C-labeled cpd, cinnamic acid, 2-(14)C-labeled cpd, cinnamic acid, 3-(14)C-labeled cpd, cinnamic acid, 3H-labeled cpd (E)-isomer, cinnamic acid, 3H-labeled cpd (Z)-isomer, cinnamic acid, ion(1-), cinnamic acid, ion(1-)-(E)-isomer, cinnamic acid, nickel (+2) salt, cinnamic acid, potassium salt, cinnamic acid, sodium salt, cinnamic acid, sodium salt(E)-isomer, cinnamic acid, sodium salt(Z)-isomer, cinnamic acid, zinc salt(E)-isomer

Depositor-Supplied Synonyms

CINNAMIC ACID, TRANS-CINNAMIC ACID, 3-Phenylacrylic acid, 140-10-3, (E)-Cinnamic acid, Phenylacrylic acid, trans-3-Phenylacrylic acid, Zimtsaeure, Cinnamylic acid, 621-82-9, 3-Phenylpropenoic acid, Benzenepropenoic acid, (E)-3-phenylprop-2-enoic acid, trans-beta-Carboxystyrene, (E)-cinnamate, 3-phenylprop-2-enoic acid, 3-Phenyl-2-propenoic acid, trans-Cinnamate, Benzylideneacetic acid, 2-Propenoic acid, 3-phenyl-, Cinnamic acid, (E)-, (E)-3-Phenyl-2-propenoic acid, trans-3-Phenyl-2-propenoic acid, (2E)-3-phenylprop-2-enoic acid, E-Cinnamic Acid, Kyselina skoricove, Acidum cinnamylicum, Benzeneacrylic acid, beta-Phenylacrylic acid, Zimtsaeure [German], Cinnamic acid (natural), NSC 9189, trans-3-Phenylpropensaeure, (E)-3-Phenylacrylic acid, Kyselina skoricove [Czech], 2-Propenoic acid, 3-phenyl-, (E)-, (2E)-3-phenylacrylic acid, UNII-U14A832J8D, FEMA No. 2288, Isocinnamic acid, CCRIS 3190, CHEBI:35697, WBYWAXJHAXSJNI-VOTSOKGWSA-N, (2E)-3-Phenyl-2-propenoic acid, PHENYLETHYLENECARBOXYLIC ACID, EINECS 205-398-1, EINECS 210-708-3, NSC 44010, BRN 0507757, BRN 1905952, NCGC00165979-01, AI3-00891, AI3-23709, DSSTox_CID_2489, DSSTox_RID_76603, DSSTox_GSID_22489, (E)-3-phenylprop-2-enoate, CAS-140-10-3, .beta.-Phenylacrylic acid, trans-Zimtsaeure, t-Cinnamic acid, 2-Propenoic acid, 3-phenyl-, (2E)-, trans cinnamic acid, Cinnamic acid, E-, trans-b-Carboxystyrene, PhCH=CHCO2H, trans-3-Phenylacrylate, (E)-3-Phenylacrylate, PubChem13612, 63938-16-9, E-3-phenylpropenoic acid, bmse000124, AC1L9GI1, AC1Q5T9E, AC1Q71HQ, SCHEMBL1332, trans-.beta.-Carboxystyrene, WLN: QV1U1R, (E)-3-phenyl-acrylic acid, 3-Phenyl-2-propenoic acide, 3-phenyl-2E-propenoic acid, C80857_ALDRICH, trans-3-Phenyl-2-propenoate, BIDD:ER0586, CHEMBL27246, W228818_ALDRICH, W228826_ALDRICH, tert-.beta.-Phenylacrylic acid, (2E)-2-Phenyl-2-propenoate, (2E)-3-Phenyl-2-propenoate, 133760_ALDRICH, GTPL3203, 96340_FLUKA, CHEBI:27386, HMDB00930, NSC9189, MolPort-000-881-745, U14A832J8D, (2E)-2-Phenyl-2-propenoic acid, 538-42-1 (hydrochloride salt), 9045-22-1, NSC-9189, NSC44010, STR00363, 16089-48-8 (potassium salt), Tox21_112279, Tox21_302137, AR-1F5017, NSC-44010, NSC623441, SBB028745, STK286093, AKOS000118871, CCG-214473, LS-2626, LS00072, NE10311, NSC-623441, RP17351, RTR-005227, RTR-021011, NCGC00255114-01, 4CN-0914, 63938-16-9 (nickel(+2) salt), AJ-68078, AK-47839, AK114507, AN-21994, AN-23168, BP-20203, KB-61966, KB-76099, LS-54015, M182, SC-24646, ST097455, AB1002037, DB-003797, TR-005227, TR-021011, FT-0623829, FT-0655071, N1877, ST24024695, C00423, C10438, AB00374254-03, 4-09-00-02002 (Beilstein Handbook Reference), A833631, 3B4-1385, I01-8768, S01-0256, 1BE36587-A165-4142-9340-18FFE3E03426, InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6

Removed Synonyms

Tributyltin, Cinnamic acid, ion(1-), -3-phenylprop-2-enoicacid, 2-Propenoic acid, (E)-, cinnamic acid, (Z)-isomer, Cinnamic acid, potassium salt, 4-CARBOXYCINNAMIC ACID, cinnamic acid, 13C-labeled cpd, cinnamic acid, 14C-labeled cpd, cinnamic acid, nickel (+2) salt, CINNAMIC ACID, SODIUM SALT, cinnamic acid, zinc salt(E)-isomer, cinnamic acid, (trans)-(E)-isomer, c0353, c0636, CID444539, cinnamic acid, ion(1-)-(E)-isomer, cinnamic acid, sodium salt(E)-isomer, cinnamic acid, sodium salt(Z)-isomer, cinnamic acid, 2-(13)C-labeled cpd, cinnamic acid, 2-(14)C-labeled cpd, cinnamic acid, 3-(14)C-labeled cpd, cinnamic acid, 3H-labeled cpd (E)-isomer, cinnamic acid, 3H-labeled cpd (Z)-isomer, cinnamic acid, 14C-labeled cpd (E)-isomer, T1240, C029010, ACN-035587 140-10-3, TCA, 6099-03-2, 6324-79-4, CIN

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