Synthesis of cinnamyl chloride

Preparation of cinnamyl chloride

Cinnamyl chloroanhydride is prepared similarly to phenylacetyl chloride or benzoyl chloride.

Preparation of cinnamyl chloride

Preparation of cinnamyl chloride

10 g of oxalyl chloride and 10 g of sodium cinnamate with 20-30 ml of dry benzene as a solvent are placed in the reaction flask. the mixture is refluxed, and it gradually turns yellow. 6 g or 63 % of the cinnamyl chloride are obtained with melting point 35-33° C. The reaction product could be additionally purified by crystallizing from carbon tetrachloride. According to the literature the melting point of cinnamyl chloride is 35-36° C.

Oxalyl chloride and oxalyl bromide as reagents in organic chemistry, L.H. Ulich, 26, 1918

IUPAC Name

3-chloroprop-1-enylbenzene

InChI

InChI=1S/C9H9Cl/c10-8-4-7-9-5-2-1-3-6-9/h1-7H,8H2

InChI Key

IWTYTFSSTWXZFU-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CCCl

Depositor-Supplied Synonyms

Cinnamyl chloride, 3-Phenyl-2-propenyl chloride, (Chloromethyl)styrene, (3-Chloroprop-1-enyl)benzene, NSC 5599, EINECS 220-246-4, 2687-12-9, Benzene, (3-chloro-1-propenyl)-, AI3-01855, 3-Chloro-1-phenylpropene, 1-Phenyl-3-chloro-1-propene, Propene, 3-chloro-1-phenyl-, 1-Propene, 3-chloro-1-phenyl-, Benzene, (3-chloro-1-propen-1-yl)-, (3-Chloropropenyl)benzene, ACMC-1CUIK, AC1L3RTB, 3-chloroprop-1-enylbenzene, KSC491C6F, (3-chloro-1-propenyl)benzene, 1-chloro-3-phenyl-2-propene, CTK3J1162, IWTYTFSSTWXZFU-UHFFFAOYSA-N, ANW-13761, Benzene, (3-chloropropenyl)- (8CI), MCULE-2113007879, LS-29550

Removed Synonyms

Chloromethylstyrene, Chloromethyl styrene, Cyclopenta(cd)pyrene, Benzene, (3-chloropropenyl)-, CID94242

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