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Issue 56, 2014
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Base-catalyzed retro-Claisen condensation: a convenient esterification of alcohols via C–C bond cleavage of ketones to afford acylating sources

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Abstract

The base-catalyzed esterification of alcohols via retro-Claisen condensation has been demonstrated for the first time. A variety of alcohols including aryl- and heteroaryl methanols as well as aliphatic ones underwent efficient acylation to give the ester products in reasonable to good yields upon isolation. Not only conventional 1,3-diketones but also strong electron-withdrawing group containing acetophenones could serve as the acylating suppliers. The synthetic protocol is operationally simple and adaptable to a broad substrate scope. It complements the existed esterification via the retro-Claisen condensation, and enlarges this benign synthetic methodology.

Graphical abstract: Base-catalyzed retro-Claisen condensation: a convenient esterification of alcohols via C–C bond cleavage of ketones to afford acylating sources

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Publication details

The article was received on 16 May 2014, accepted on 19 Jun 2014 and first published on 23 Jun 2014


Article type: Paper
DOI: 10.1039/C4RA04618H
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Citation: RSC Adv., 2014,4, 29502-29508
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    Base-catalyzed retro-Claisen condensation: a convenient esterification of alcohols via C–C bond cleavage of ketones to afford acylating sources

    F. Xie, F. Yan, M. Chen and M. Zhang, RSC Adv., 2014, 4, 29502
    DOI: 10.1039/C4RA04618H

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