The chemistry of reactive lignin intermediates. Part 3. Products of addition of methanol and water to vinyl-substituted quinone methides

Abstract

The isomeric ethers 2,6-dimethyl-4-(1-methoxyprop-2-enyl)phenol and 2,6-dimethyl-4-(3-methoxyprop-1-enyl)phenol and the corresponding isomeric alcohols have been isolated from the reactions of 4-allylidene-2,6-dimethylcyclohexa-2,5-dienone (1a) with methanol and water. The isomer ratios for the reactions in acidic, neutral, and basic solution are reported, together with rate data for the reactions in methanol.