Synthesis of 2,6-Dimethoxy-p-aminophenol from Hardwood Lignin.

Abstract

Although the multiple functional groups in biomass offer notable chances for producing high-value chemicals, most of the current studies focused on the (deep) defunctionalization of biomass and its derivates. Herein, we present a catalytic approach to valorize birch wood lignin with maintaining the methoxy and hydroxy groups in the final product (i. e., 2,6-dimethoxy-p-aminophenol), which has applications in different sectors such as pharmaceuticals. The proved approach involves four steps with a high yield (19.8 wt % on the basis of used lignin) to 2,6-dimethoxy-p-aminophenol. The native lignin in birch wood was first converted using alkaline aerobic oxidation in the presence of copper ions toward high-yield syringaldehyde, which was then selectively oxidized toward 2,6-dimethoxy-1,4-benzoquinone using H2 O2 and V2 O5 . Oximation of 2,6-dimethoxy-1,4-benzoquinone can selectively form 2,6-dimethoxy-1,4-benzoquinone-4-oxime, which can be quantitatively hydrogenated toward 2,6-dimethoxy-p-aminophenol. This work highlights the unique potential of biomass and its derivates for the sustainable production of high-value products with exploring the value of inherent functional groups.