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

J Kwiatkowski, J Majer, P Kwiatkowski, J Jurczak

Index: Kwiatkowski, Jacek; Majer, Jakub; Kwiatkowski, Piotr; Jurczak, Janusz Synthesis, 2008 , # 20 p. 3237 - 3244

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Abstract

Abstract Direct synthesis of racemic aromatic α-hydroxyacetic acid esters via Friedel-Crafts reaction of nonactivated, simple arenes with ethyl glyoxylate promoted by SnCl 4 or AlCl 3 is described. The use of SnCl 4 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 ...