Collect. Czech. Chem. Commun. 1992, 57, 119-122

An Anomalous Course of the Darzens Reaction Catalyzed with Magnesium Methoxide

Jiří Svoboda, Miloslav Nič and Jaroslav Paleček

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


The reaction of benzaldehyde with methyl chloroacetate catalyzed with magnesium methoxide gave beside the expected methyl 2,3-epoxy-3-phenylpropanoate (I) also comparable amounts of methyl 2-hydroxy-3-methoxy-3-phenylpropanoate (II). The condensation was accompanied by a competing disproportionation of benzaldehyde giving methyl benzoate and benzyl alcohol. The course of the condensation reaction is discussed.