The Reformatsky Reaction with 2-Hydroxymethylenecyclohexanone. 5, 6, 7, 8-Tetrahydrocoumarin1

AS Dreiding, AJ Tomasewski

Index: Dreiding; Tomasewski Journal of the American Chemical Society, 1954 , vol. 76, p. 6388,6391

Full Text: HTML

Citation Number: 9

Abstract

The Reformatsky reaction of 2-hydroxymethylenecyclohexanone (11) with methyl bromoacetate produced a 25% yield of 5, 6, 7, 8-tetrahydrocoumarin (I) and a 30% yield of a diene-diester fraction. The structure of I was proven by its conversion with alkali to~-(2- ketocyclohexylidene)-propionic acid (VII, R= H) under mild conditions and to cyclohexanone under stronger conditions. Saponification of the diene-diester fraction gave~-(2- ...