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

Jacek Kwiatkowski; Jakub Majer; Piotr Kwiatkowski; Janusz Jurczak

doi:10.1055/s-0028-1083154

PAPER

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

Jacek Kwiatkowski^a, Jakub Majer^a, Piotr Kwiatkowski^a, 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;

Abstract

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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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