Ethanol → Ethyl 3-[4-(trifluoromethyl)phenyl]prop-2-enoate

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:21]([O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:13][CH:12]=1)[CH3:22]

Participants

Reactant 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

Product 1

HCID 53662772Ethyl 3-[4-(trifluoromethyl)phenyl]prop-2-enoate

Procedure

A suspension of 300 g of 4-trifluoromethylcinnamic acid (J. Org. Chem. 43:980 (1980) and 25 ml of concentrated sulfuric acid in 1.7 liters of ethanol is heated to reflux for 24 hours. The solution is concentrated, cooled, and filtered to give as a white solid, 4-trifluoromethylcinnamic acid ethyl ester, mp 40°-41° C.