AN INTERMOLECULAR MICHAEL ADDITION OF BENZENE

The first intermolecular Michael addition of benzene leading to the fo rmation of 3,3-diphenylpropionanilide is described. 2-Methoxyaninline was reacted with cinnamoyl chloride to give 2-methoxycinnamanilide (1) which was treated with aluminum chloride in benzene at 80 degrees C t o afford 2'-hydroxy-3,3-diphenylpropionanilide (4) in an 85% overall y ield. Accordingly, 4'-hydroxy-2'-metbyl-3,3-diphenylpropionanilide (6) was prepared from 4-methoxy-2-methylcinnamanilide (5) in 76% yield. C opyright (C) 1996 Elsevier Science Ltd