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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

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Received: 5 April 2011; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA 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(5):3845-3854.

Chicago/Turabian Style

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.


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