The Synthesis of Hydroxybenzaldehydes from Bromobenzaldehydes via Lithiated Schiff's Bases. Preparation of 5-Hydroxypiperonal and Related Compounds

Abstract

Myristicinaldehyde (3-methoxy-4, 5-methylenedioxy-benzaldehyde) and 3,4,5-trimethoxybenzaldehyde are intermediates in the synthesis of numerous alkaloids and pharmacological agents. As a part of our studies on the synthesis and pharmacological action of ring-substituted phenethylamines, we had need of a general method for the preparation of the 3-alkoxy homologs of these two aldehydes. The published syntheses of myristicinaldehyde generally utilized myristicin (3-methoxy-4,s-methylenedioxyallylbenzene) as a starting material, which is readily available only from botanical sources; 3,4,5-trimethoxybenzaldehyde is usually prepared by the methylation and reduction of gallic acid. Consequently, the 3-alkyl homologs are not readily synthesized from these natural products and have not been reported in the literature.