The Nitration of 4-Methylphenol, 3,4-Dimethylphenol and 3,4,5-Trimethylphenol With Nitrogen Dioxide

Abstract

Reaction of 4-methylphenol (la) with excess nitrogen dioxide in either benzene or dichloromethane gives the 4-nitro dienone (2a) and the 2,6-dinitrophenol (5). Similar reactions of 3,4-dimethylphenol (Ib) yields the 4-nitro dienone (2b), the 2,6-dinitrophenol (8) and the 4-hydroxy 2,6-dinitro dienone (9), while reaction of 3,4,5-trimethylphenol (1c) gives the 4-nitro dienone (2c), the 2,4-dinitro dienone (11) and the 2,4,6-trinitro dienone (12a). The reaction pathways by which these products are formed are described and the results of reactions of postulated intermediates with nitrogen dioxide presented.