The Chlorination of 2-Tert-Butyl-4,6-Dimethylphenol and 2,6-Di-Tert-Butyl-4-Methylphenol. The Formation of 5,6-Dichloro-4-Methylenecyclohex-2-Enones

Abstract

The chlorination in acetic acid of 2-t-butyl-4,6-dimethylphenol (1) gives two chloromethylene compounds (4) and (5), and trichloro ketones (6) and (7). In contrast, 2,6-di-t-butyl-4-methylphenol (2) gives six chlorination products (14)-(19). The notable feature of the reactions is the modification of the 4-methyl groups of the phenols (1) and (2). The modes of formation of all reaction products are described. X-ray structure determinations are reported for compounds (5),(6),(15),(17), (19) and (21).