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Selective Monoesterification of Malonic Acid Catalyzed by Boric Acid

Stephan M. Levonis ^A , Laurent F. Bornaghi ^A and Todd A. Houston ^A ^B

+ Author Affiliations

- Author Affiliations

^A Institute for Glycomics, Gold Coast Campus, Griffith University, Qld 4222, Australia.

^B Corresponding author. Email: t.houston@griffith.edu.au

Australian Journal of Chemistry 60(11) 821-823 https://doi.org/10.1071/CH07231
Submitted: 4 July 2007 Accepted: 22 August 2007 Published: 1 November 2007

Abstract

Boric acid catalyzes the monoesterification of malonic acid, likely through a chelation mechanism that is not available to the monoester product. Under more forcing conditions, diesters form to some extent, but conditions can be optimized to favour the monoester product (56–80%). With the easily handled solid acid catalyst, these reactions can be run with excess alcohol as solvent or with stoichiometric amounts of alcohol in acetonitrile with moderate heating.

Acknowledgement

We thank the Institute for Glycomics and Griffith University for financial support. We are also grateful to Dr Sally-Ann Poulsen and Mr. Hoan The Vu (Eskitis Institute for Cell and Molecular Therapies, Griffith University) for high-resolution mass spectrometry data.

References

[1] (a) Jencks W. P., Catalysis in Chemistry and Enzymology 1969, pp. 30–36 (McGraw-Hill: New York).
       (b) P. J. Duggan, E. M. Tyndall, J. Chem. Soc., Perkin Trans. 1 2002, 1325.
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