Next Article in Journal
RuCl3·3H2O Catalyzed Reactions: Facile Synthesis of Bis(indolyl)methanes under Mild Conditions
Previous Article in Journal
Synthesis of Homoveratric Acid-Imprinted Polymers and Their Evaluation as Selective Separation Materials
Molecules 2011, 16(5), 3845-3854; doi:10.3390/molecules16053845

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
Download PDF [158 KB, uploaded 18 June 2014]


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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert