Nitration of some derivatives of vanillic and veratric acids

Abstract

The behaviour of methyl 4 - acetoxy - 3 - methoxybenzoate and methyl 3,4 - dimethoxybenzoate with nitric acid have been examined and compared. With methyl 4 - acetoxy - 3 - methoxybenzoate, only the 2 - nitro product was observed while with methyl 3,4 - dimethoxybenzoate, the 6 - nitro product was isolated. This has been rationalised by invoking a co-ordination mechanism. The effect of the nitration medium was also studied. Studies of the nitration of some methyl esters of vanillic acid in which the 4 - hydroxyl group had been esterified with various acyl groups have also been carried out, and again, the products of nitration in the 2 - position were found to predominate.