Preparation of 2-alkoxy-5-methoxybenzaldehydes and 2-ethoxy-5- alkoxybenzaldehydes

Abstract

Direct O-alkylation of 2-hydroxy-5-methoxybenzaldehyde (1) with alkyl bromides or iodides gave nine 2-alkoxy-5-methoxybenzaldehydes 2a-i in high yields, six of which are novel compounds. Treatment of 2-ethoxy-5- bromobenzaldehydes (3) with n-BuLi, morpholine and nitrobenzene afforded 2-ethoxy-5-hydroxybenzaldehyde (4), which easily underwent O-alkylation to furnish 2-ethoxy-5-alkoxybenzaldehydes 5a-b in total moderate yields.