Methanol → HCID 12917671, compound

Participants

Reaction Conditions

Reaction Steps

Water (2 ml) and 4 ml of methanol were added to 420 mg of methyl α-(p-isobutylphenyl)-α-(methylthio)propionate. Then, 280 mg (85% content) of potassium hydroxide was added, and the mixture was stirred at 60° C. for 2.5 hours. The reaction mixture, initially heterogeneous, became uniform. Water (30 ml) was added, and the mixture was extracted with 10 ml of methylene chloride. The aqueous layer was acidified with conc. hydrochloric acid to a pH of 1, and extracted three times with 20 ml of diethyl ether. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the diethyl ether. Thus, 394 mg of crude α-(p-isobutylphenyl)-α-(methylthio)propionic acid was obtained as an oil in a yield of 99%. The oil soon crystallized, and recrystallization from water/methanol afforded colorless crystals having a melting point of 89° to 92° C.

Provenance & Evidence