Acrylonitrile → 4-(Dimethylamino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 53 g of acrylonitrile and 1.0 g of copper(II) acetate in 100 g of o-xylene was heated to the boil (85° C.), after which a solution of 82 g of p-dimethylaminobenzaldoxime in 110 g of o-xylene was added dropwise by heating further. During the addition, the boiling point of the reaction mixture increased to 135° C. The mixture was stirred under reflux for a further 30 minutes and was then left to cool. The precipitated acrylamide was filtered off under suction, and the mother liquor was extracted by shaking with a little water. The organic phase was evaporated down and the residue was taken up in 400 ml of petroleum ether. After the mixture had been left to stand overnight at 0° C., 66 g (90%) of p-dimethylaminobenzonitrile were obtained in the form of yellow crystals of melting point 75°-76° C.

Provenance & Evidence