Ethanol → 2-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzoic acid

Reaction equation

[CH3:1][CH:2]([S:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10]C=1C#N)[CH2:3][CH3:4].[OH-:18].[Na+].[CH2:20]([OH:22])[CH3:21]>O>[CH3:1][CH:2]([S:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:21]=1[C:20]([OH:18])=[O:22])[CH2:3][CH3:4]

Participants

Procedure

A solution of 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzonitrile (8.6 g) in ethanol was added to a solution of sodium hydroxide (47.3 g) in water and the resultant mixture was heated at reflux for 24 hours. It was poured into water and acidified to pH 1. The mixture was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzoic acid (8.1 g) as a white solid, m.p. 99.8°-101° C.