The Chlorination of Some Substituted 2,4-Dimethylphenols

Abstract

Chlorination reactions of 2-chloro-3,4,6-trimethylphenol (4), 2-chloro-4,6-dimethylphenol (5) and 3-chloro-2,4,6-trimethylphenol (6) are described. In acetic acid or acetic anhydride solution, chlorinations yield predominantly the corresponding 4-chlorocyclohexa-2,5-dienones (8), (17a) and (29), but in carbon tetrachloride containing pyridine products are formed which result from the modification of the 4-methyl group in each substrate. X-Ray crystal structure analyses are reported for compounds (7), (14), (28) and (31).