The Chlorination of 2-t-Butyl-4-chloro-6-methylphenol. Some Reactions of Chlorine and Nitrogen Dioxide With 6-Chlorocyclohexa-2,4-dienones Derived From 2-t-Butyl-4-chloro-6-methylphenol

Abstract

Chlorinations of 2-t-butyl-4-chloro-6-methylphenol(10) and of the mixture of 4,6-dichlorocyclo-hexa-2,ddienones (11) and (12) give the tetrachloro ketones (13)-(15). Reaction of the dichlorocyclohexa-2,4-dienone mixture with nitrogen dioxide gives predominantly dichloro dinitro ketones (17) which rearrange on chromatography to yield the hydroxy dienone (21). X-Ray crystal structures are reported for compounds (13)-(15), (20) and (21).