Methylation of substituted 1,4-benzoquinones

Abstract

Methylation of 1,4-benzoquinones I and Ia with diazomethane afforded methyl 15-(6-methoxy-3-methyl-1,4-benzoquinon-2-yl)pentadecanoate (IIa) and methyl 15-(3-methoxy-2,5-dioxobicyclo[4.1.0]hept-3-en-1-yl)pentadecanoate (IIIa), methylation of 1,4-benzoquinone IVa led to methyl 15-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)pentadecanoate (Va) and methyl 15-(3,4-dimethoxy-6-methyl-2,5-dioxobicyclo[4.1.0]hept-3-en-1-yl)pentadecanoate (VIa). Structure of the products was established by spectral methods.