Some dimeric by-products of the preparation of 2,4-dimethoxybenzyl cyanide from 2,4-dimethoxy-β-nitrostyrene

Abstract

Catalytic reduction of 2,4-dimethoxy-β-nitrostyrene over palladised charcoal affords principally 2,4-dimethoxy-phenylacetaldehyde oxime. One of the by-products is meso-αα′-bis-(2,4-dimethoxyphenyl)succinaldehyde dioxime. When the crude hydrogenation product reacts with acetic anhydride it affords principally 2,4-dimethoxybenzyl cyanide, but αα′-bis-(2,4-dimethoxyphenyl)fumarodinitrile and trans-2,2′,4,4′-tetramethoxystilbene are also formed. We describe the preparation of cis-erythro-2,3-diphenylbutan-4-olide.