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Synthesis 2008(20): 3237-3244  
DOI: 10.1055/s-0028-1083154
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Jacek Kwiatkowskia, Jakub Majera, Piotr Kwiatkowskia, Janusz Jurczak*a,b
a Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
b Department of Chemistry, University of Warsaw, 02-093 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: jurczak@icho.edu.pl;
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Publikationsverlauf

Received 24 March 2008
Publikationsdatum:
25. September 2008 (online)

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Abstract

Direct synthesis of racemic aromatic α-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.

Key words

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

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