Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation

被引：6

作者：

Adogla, Enoch A. ^{[1
]}

Janser, Romy F. J. ^{[1
]}

Fairbanks, Samuel S. ^{[1
]}

Vortolomei, Caitlyn M. ^{[1
]}

Meka, Ranjith K. ^{[1
]}

Janser, Ingo ^{[1
]}

机构：

[1] New Mexico Inst Min & Technol, LOSCB, Dept Chem, Socorro, NM 87801 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 01期

基金：

美国国家卫生研究院;

关键词：

Friedel-Crafts; Fries rearrangement; Selective methoxy cleavage; Selective acylation; Ethacrynic acid; Substituted catechols; TRANSFERASE P1-1 ACTIVITY; PROTECTING GROUPS; DERIVATIVES;

D O I：

10.1016/j.tetlet.2011.10.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Friedel-Crafts reaction of 2,6-dimethoxyphenol in the presence of aluminum chloride and propanoyl or butanoyl chloride, respectively, lead, at elevated temperatures, to a selective cleavage of one of the methoxy groups followed by a selective acylation of the meta position with respect to the phenolic hydroxyl group. Under the same reaction conditions 2-methoxyphenol does not get demethylated; a mechanism to account for these findings is proposed. This reaction gives access to a variety of ortho-acylated catechols. Substituted catechols are widely used in supramolecular chemistry and are precursors of pesticides, flavors, and fragrances. Additionally, catechol moieties are found in various natural products. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：11 / 14

页数：4

共 14 条

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