Selective monoesterification of malonic acid catalyzed by boric acid

Stephan M. Levonis; Laurent F. Bornaghi; Todd A. Houston

doi:10.1071/CH07231

Selective monoesterification of malonic acid catalyzed by boric acid

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › Research › peer-review

29 Citations (Scopus)

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.

Original language	English
Pages (from-to)	821-823
Number of pages	3
Journal	Australian Journal of Chemistry
Volume	60
Issue number	11
DOIs	https://doi.org/10.1071/CH07231
Publication status	Published - 2007
Externally published	Yes

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title = "Selective monoesterification of malonic acid catalyzed by boric acid",

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.",

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AU - Bornaghi, Laurent F.

AU - Houston, Todd A.

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N2 - 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.

AB - 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.

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DO - 10.1071/CH07231

M3 - Article

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JO - Australian Journal of Chemistry

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Selective monoesterification of malonic acid catalyzed by boric acid

Abstract

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