Sodium Cyanide → Ethyl 3-(cyanomethyl)benzoate

Participants

Reaction Steps

To a solution of ethyl 3-(chloromethyl)benzoate (5.0 g, 25.1 mmol) in dimethylsulfide (50 mL) was added sodium cyanide (1.85 g, 37.8 mmol), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, and the extract was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (4.23 g, 89%) as a colorless oil.

Provenance & Evidence