Qi‐xue Qin, J. Yang, Duo-Zhi Chen
Jun 24, 2013
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Influential Citations
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Journal
Organic Preparations and Procedures International
Abstract
Of the many methods for its preparation,8–11 the simplest employs the Baeyer-Villiger rearrangement of commercially available and expensive 3,4,5-trimethoxybenzaldehyde followed by hydrolysis to produce 4 in 46% yield. However, the reaction conditions are very harsh and employ catalysts or reagents that are toxic and environmentally unfriendly. The methylation of 2,6-dimethoxyhydroquinone also gave 4 albeit in poor yields (<5%) because of the poor regioselectivity of the reaction as would be expected.12 More recently, inexpensive and commercially available 3,4,5-trimethoxybenzoic acid (1) has been used as a source of 4 via substitutive ipso nitration to 3,4,5-trimethoxynitrobenzene followed by reduction to the aniline, diazotization and hydrolysis.13 As part of our program for the development of natural biological compounds and in the investigation on their structure-activities relationships,14,15 we now report an alternative and efficient process to