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Molecules 2011, 16(5), 3845-3854; doi:10.3390/molecules16053845
Article

Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates

, , *  and
College of Life Science and Bio-engineering, Beijing University of Technology, Pingleyuan Street Number 100, Chaoyang District, Beijing 100124, China
* Author to whom correspondence should be addressed.
Received: 5 April 2011 / Revised: 15 April 2011 / Accepted: 18 April 2011 / Published: 6 May 2011
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Abstract

A simple, efficient and eco-friendly procedure for the selective monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates under quaternary ammonium salt catalysis conditions is presented. The catalytic activities of various quaternary ammonium salts were investigated using different molar ratios of NaOH and water-organic solvent mixtures. The results indicate that the combination of 1.0 equivalent of tetraethyl-ammonium bromide (TEAB) with 1.2 equivalents of NaOH in a 10% water-ethanol media at 40 °C displays remarkable selectivity for the monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates. The utility of this process is demonstrated by the monohydrolysis of a series of 4-aryl-4H-pyran-3,5-dicarboxylate esters to afford the corresponding monoesters in 20–80% yields under the optimized conditions.
Keywords: monohydrolysis; 4-aryl-4H-pyran; quaternary ammonium salt; monoester; symmetric diester monohydrolysis; 4-aryl-4H-pyran; quaternary ammonium salt; monoester; symmetric diester
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Duan, J.; Song, X.; Yan, H.; Song, X. Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates. Molecules 2011, 16, 3845-3854.

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