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Synfacts 2008(5): 0540-0540  
DOI: 10.1055/s-2008-1072557
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Monoesterfication of Alkylphosphonic Acids by DCC-Celite

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
A. K. Gupta, R. Kumar, H. K. Gupta, V. Tak, D. K. Dubey*
Defence R&D Establishment, India
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

A solvent-free synthesis of O-alkyl hydrogen alkyl phosphonates was described. Thus, the reaction of alkylphosphonic acids and alcohols (1 mol equiv) with DCC-Celite (2 mol equiv) was carried out at room temperature to 60 °C to give the corresponding monoesters in 80-92% yield (15 examples). The monoesterification with primary and secondary alcohols was completed within 30-45 and 45-60 min, respectively, while tertiary alcohols did not react with alkylphosphonic acids under similar conditions.