Simple and Efficient Synthesis of Racemic Substituted Mandelic Acid Esters from Nonactivated Arenes and Ethyl Glyoxylate

被引：4

作者：

Kwiatkowski, Jacek ^{[1
]}

Majer, Jakub ^{[1
]}

Kwiatkowski, Piotr ^{[1
]}

Jurczak, Janusz ^{[1
,2
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland

来源：

SYNTHESIS-STUTTGART | 2008年 / 20期

关键词：

arenes; Friedel-Crafts hydroxyalkylation; ethyl glyoxylate; alpha-hydroxy esters; Lewis acids; mandelic acids;

D O I：

10.1055/s-0028-1083154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct synthesis of racemic aromatic a-hydroxyacetic acid esters via Friedel-Crafts reaction of nonactivated, simple arenes with ethyl glyoxylate promoted by SnCl4 or AlCl3 is described. The use of SnCl4 opens a fast access to various alkyl- and aryl-substituted mandelic acids esters at room temperature within two hours in good yield (>80%) and with high regioselectivity. The procedure was successfully employed also for the alkylation of compounds with condensed aromatic rings. Alternative hydroxyalkylations with AlCl3 require longer reaction time and higher temperature to get a good yield.

引用

页码：3237 / 3244

页数：8

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