Carbon Tetrachloride → 4-(Trichloromethyl)benzonitrile

Participants

Reaction Steps

p-Tolunitrile (4.10 g, 0.035 mole) and dichlorine monoxide (6.93 g, 0.074 mole) in carbon tetrachloride (97 ml) were added to a bottle under nitrogen. The bottle was capped and stored at room temperature for 4 days. The water layer was separated, the organic layer dried (MgSO4) and the solvent removed on a rotary evaporator to give p-cyanobenzotrichloride as an oil (7.87 g, yield 100%). The oil was combined with a similar run and distilled in a short path still to give a white crystalline solid which was recrystallized from petroleum ether to give substantially pure p-cyanobenzotrichloride (mp 40.5°-41.7°).

Provenance & Evidence