Hydrochloric Acid → N-Phenylacrylamide

Participants

Reaction Conditions

Reaction Steps

7.2 parts 30% methanolic Na-methylate solution are added to 46.5 parts aniline. 77 parts 2-carbomethoxy-7-oxabicyclo(2,2,1)hept-5-ene are added drop-wise at 40° C. The reaction medium is then stirred for 15 hours at this temperature and neutralised with 4 parts concentrated hydrochloric acid. 50 parts water are added, and the organic phase separated off. The organic phase is reduced in a rotary evaporator at a bath temperature of 90° C. and under a vacuum of 20 Torr. The residue is heated in a vacuum of 20 Torr to 110° to 120° C. (bath temperature 140° C.). On conclusion of the furane separation, the sedimentation temperature increases and the product distills over. 27.5 parts N-phenylacrylamide with a boiling point of 135° C. at 0.4 Torr are obtained. The product recrystallised from the acetonitrile at -20° C. has a melting point of 114° to 115° C.

Provenance & Evidence