Reaction of Phosphoryl Chloride-Formamide Adduct with Alkylphenols

Abstract

When POCI₃-NH₂CHO adduct was allowed to react with p-cresol and its derivatives (o-methyl-, o-t-butyl-, o-bromo-) in formamide at 100-120°C, N-f ormy1-6, 12-epimino-2, 10-dimethy1-6 H, 12 H-dibenzo [d, g][1, 3]dioxocins [1a-d] were formed. Acid treatment of [1a] at a room temperature gave N-formyl-1, 1-bis (2-hydroxy-5-methylphenyl) methylamine [2a], and hydrolyiis of [1a] at 50-60°C for 8 hr afforded 1, 1Lbis (2-hydroxyL5Lmethylphenyl) methylamine [3a] which was identical with the product obtained by the reduction of 2, 2′-dihydroxy-5, 5′-dimethylbenzophenone oxime, When [2a] or [3a] was allowed. kto react with POCI₃-NH₂CHO adduct in formamide, [1a] was formed. Structure of dibromo compound [1d] was Confirmed by X-ray crystal refraction.