Reactions of 2-ethynyl-2-hydroxy-1,3-dimethylcyclohexanecarboxylic acid

Abstract

2-Ethynyl-2-hydroxy-1,3-dimethylcyclohexanecarboxylic acid has been synthesised and its reduction and its reactions with acidic and mercury catalysts and with other reagents have been studied. Some reactions of this and related compounds involve molecular rearrangements including an α-ketol ring enlargement, and steric hindrance of the functional groups is often manifest. Some infrared and n.m.r. data are given; several of the acids and esters encountered show abnormal infrared frequencies.