Benzene → 3-(4-Chlorophenyl)-3-methylpentan-2-one

Participants

Reaction Steps

To a solution of 2-(4-chlorophenyl)-2-methylpropionitrile (243 mg, 1.4 mmol) in benzene (1.4 mL) was added slowly at 50° C. under an atmosphere of nitrogen and with stirring to a 2.8 M solution of ethylmagnesium chloride in tetrahydrofuran (1.45 ml, 4.1 mmol). The reaction mixture was heated to reflux for 2 h, and thereafter, cooled and poured onto 10% aqueous ammonium chloride solution (4 mL). The organic layer was separated and treated with 2 N aqueous hydrochloric acid solution (1 mL). The reaction was heated to reflux for 1 h. After cooling the reaction mixture was diluted with water and extracted twice with benzene. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (9:1 v/v) as eluent to give the title compound (64 mg, 20%) as a pale-yellow oil.

Provenance & Evidence