Methanol → 2-Isopropyl-4-(4-fluorophenyl)-3-butenoic acid

Reaction equation

[CH:1]([CH:4]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]([O:7]CC)=[O:6])([CH3:3])[CH3:2].[OH-].[K+].CO>O>[CH:1]([CH:4]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2]

Participants

Procedure

A mixture of the above ester (0.46 g), potassium hydroxide (2.5 mmol), 3 ml methanol and 0.5 ml water is stirred at about 45° overnight. Methanol is removed by evaporation and then 5% NaOH-ether is added. After adjusting to about pH 3 by addition of dilute HCl, the mixture is extracted with ether. The ether phase is washed with water and brine, dried over sodium sulfate, and solvent evaporated to yield 2-isopropyl-4-(4-fluorophenyl)-3-butenoic acid.