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Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates
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; in revised form: 15 April 2011 / Accepted: 18 April 2011 / Published: 6 May 2011
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
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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.
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(5):3845-3854.
Duan, Jiaojiao; Song, Xiaohui; Yan, Hong; Song, Xiuqing. 2011. "Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates." Molecules 16, no. 5: 3845-3854.