N-methyl-2-pyrrolidone → 4-(3-Hydroxypropyl)benzonitrile

Participants

Reaction Steps

A mixture of 4-bromobenzenepropanol (9.0 g), cuprous cyanide (4.5 g), cuprous iodide (20 mg), and N-methyl-2-pyrrolidone (20 ml) was heated at 180°-190° for 4 h and poured into a solution of ferric chloride hexahydrate (4.5 g) in hydrochloric acid (2 M; 30 ml). The mixture was heated at 70°-80° for 15 min and extracted with EA (3×100 ml). The extract was washed with hydrochloric acid (2 M; 50 ml), water (50 ml), and aqueous sodium hydroxide (2 M; 50 ml), dried and evaporated. The residue was purified by [C] eluting with cyclohexane-ER (1:1) to give the title compound (3.5 g). T.l.c. (cyclohexane-ER 1:1) Rf 0.15

Provenance & Evidence