Abstract
Anodic oxidation of 2-hydroxy-3-methoxy-5-methylbenzaldehyde (II) in acetonitrileacetic acid (3 : 1) containing sodium acetate gave an acetoxylated product in which the acetoxyl group is attached to the side-chain methyl group. On the other hand, oxidation of the Schiff bases (I) derived from II under the same conditions gave cyclohexenetriones. The latter products were shown to be formed by further oxidation of the initially formed acetoxylated Schiff bases, in which the acetoxyl group is introduced into the ring meta to the hydroxyl group.
