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Synthesis 2003(5): 0695-0698
DOI: 10.1055/s-2003-38074
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Selective and Mild Synthetic Route to Dialkyl Phosphates

Johanna M. Kuipera, Ron Hulstb, Jan B. F. N. Engberts*a
a Physical Organic Chemistry Unit, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
b Kiadis B.V., Niels Bohrweg 11-13, 2333 CA Leiden, The Netherlands
Fax: +31(50)3634296; e-Mail: J.B.F.N.Engberts@chem.rug.nl;
Further Information

Publication History

Received 28 October 2002
Publication Date:
21 March 2003 (online)

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Abstract

A very mild synthetic route to dialkyl phosphates is described. Reaction of the appropriate alcohol with PCl3 followed by treatment with pyridine and CCl4 afforded the corresponding trichloromethyl ester. Subsequent reaction with the triethylamine salt of acetic acid followed by hydrolysis of the formed mixed anhydride under very mild conditions afforded the dialkyl phosphates in high yield.

Key words

dialkyl phosphates - lipids - alcohols - dialkyl phosphonates - azobenzene

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10

Smits, E.; Wagenaar, A. unpublished results.

21

Due to the high solubility of diethyl phosphate in H2O a lower isolated yield was obtained than expected. Continuous extraction will likely increase the yield considerably.

27

Diethyl phosphate is available from Supelco.