Synthesis of cinnamic anhydride

Preparation of cinnamic anhydride

Preparation of cinnamic anhydride

Preparation of cinnamic anhydride

50 g of cinnamic acid and 200 g of acetic anhydride are boiled under a reflux condenser for six hours. The liquid is then distilled until the temperature reaches 146° C, and the residue, after cooling, taken up with ether. On evaporating off the ether, the anhydride separates in the crystalline state. It may be recrystallised from alcohol, and forms colourless needles which melt at 136° C.

Preparation of organic compounds, E. de. Barry Barnett, 174, 1912

IUPAC Name

[(E)-3-phenylprop-2-enoyl] (E)-3-phenylprop-2-enoate

InChI

InChI=1S/C18H14O3/c19-17(13-11-15-7-3-1-4-8-15)21-18(20)14-12-16-9-5-2-6-10-16/h1-14H/b13-11+,14-12+

InChI Key

FXEDRSGUZBCDMO-PHEQNACWSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CC(=O)OC(=O)C=CC2=CC=CC=C2

Isomeric SMILES

C1=CC=C(C=C1)/C=C/C(=O)OC(=O)/C=C/C2=CC=CC=C2

MeSH Synonyms

cinnamic anhydride, cinnamic anhydride, (E,E)-isomer

Depositor-Supplied Synonyms

Cinnamic anhydride, 3-Phenylacrylic anhydride, UNII-2VMI2E65WO, Cinnamic acid anhydride, 2-Propenoic acid, 3-phenyl-, anhydride, 538-56-7, EINECS 208-695-4, 21947-71-7, (2E)-3-phenylprop-2-enoyl (2E)-3-phenylprop-2-enoate, NSC-78945, (E)-Cinnamic anhydride, AC1NUXP6, 2VMI2E65WO, Cinnamic anhydride, (E,E)-, Cinnamic acid anhydride [MI], Bis(3-phenylpropenoic)anhydride, SCHEMBL9247555, NSC 78945, ZINC85773085, AKOS015994929, LP059328, OR024488, AI3-18175, FT-0632337, 2-Propenoic acid, 3-phenyl-, anhydride, (2E,2’E)-, [(E)-3-phenylprop-2-enoyl] (E)-3-phenylprop-2-enoate, 3B3-051739, (E)-3-phenyl-acrylic acid [(E)-3-phenyl-acryloyl] ester, 2-Propenoic acid, 3-phenyl-, 1,1′-anhydride, (2E,2’E)-

Removed Synonyms

CID5463289

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