4'-Cyanoacetophenone → 4-(2-Hydroxypropan-2-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of p-acetylbenzonitrile (3.0 g, 20.0 mmol) in tetrahydrofuran at −78° C. was added drop-wise a solution of 3.0 M methyl magnesium chloride in tetrahydrofuran (7.6, 23.0 mmol). The reaction mixture was stirred at −78° C. for 3 hours and then quenched with methanol added drop-wise. The reaction mixture was thereafter poured into water (200 ml), acidified with oxalic acid added portion-wise, and then extracted with diethyl ether (2×200 ml). The organic extracts were combined, washed with water (1×40 ml), brine (1×40 ml), dried over magnesium sulfate (MgSO4), and then concentrated to give an oil. The oil product was purified using chromatography on silica gel, eluting with ethyl acetate/hexane (1:5), to give 1.4 g of 4-(1-Hydroxy-1-methyl-ethyl)-benzonitrile as a clear oil.

Provenance & Evidence