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

中文翻译：

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3,4,5-三甲氧基苯酚的替代制备

在其制备的众多方法中，8-11 最简单的方法是对市售且昂贵的 3,4,5-三甲氧基苯甲醛进行 Baeyer-Villiger 重排，然后水解以 46% 的产率生产 4。然而，反应条件非常苛刻，并且使用有毒且对环境不友好的催化剂或试剂。2,6-二甲氧基氢醌的甲基化也产生了 4，尽管收率很低（<5%），因为反应的区域选择性很差，正如预期的那样。 12 最近，廉价且可商购的 3,4,5-三甲氧基苯甲酸（ 1) 已被用作 4 的来源，通过取代 ipso 硝化为 3,4,5-三甲氧基硝基苯，然后还原为苯胺、重氮化和水解。