Cleavage of the Methylenedioxy Ring in the Grignard Reaction of 3,4-Methylenedioxybenzonitrile

Abstract

The reaction of 3,4-methylenedioxybenzonitrile (2) with ethyl magnesium bromide gives products resulting from opening of the methylenedioxy ring, namely 4-hydroxy-3-n-propoxypropiophenone (3) and 3-hydroxy-4-n-propoxypropiophenone (4) in addition to the expected product 3,4-methylenedioxypropiophenone (1). The isomeric hydroxy-n-propoxy ketones were differentiated on the basis of their spectroscopic properties.