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Current Organic Chemistry

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ISSN (Online): 1875-5348

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Research Article

Alcoholysis Versus Fission of the Ester Group During the Reaction of Dialkyl Phenylphosphonates in the Presence of Ionic Liquids

Author(s): Nikoletta Harsági, Csilla Bertha, Nóra Zsuzsa Kiss, Réka Henyecz, Petra Regina Varga, Péter Ábrányi-Balogh, László Drahos and György Keglevich*

Volume 25, Issue 7, 2021

Published on: 11 February, 2021

Page: [842 - 848] Pages: 7

DOI: 10.2174/1385272825666210212115649

Abstract

In the microwave-assisted alcoholysis of dialkyl phenylphosphonates performed in the presence of suitable ionic liquids, such as [bmim][BF4] or [bmim][PF6], affording the phosphonate with mixed alkoxy groups and the fully transesterified product, the fission of the phosphonate function to the ester-acid or diacid moiety was inevitable. Moreover, in the presence of [emim][HSO4], the reaction could be performed to afford the phosphonic esteracid with a selectivity of 66% and the diacid with a selectivity of 97%. The ester-acids provided by the new protocol may be valuable intermediates.

Keywords: Dialkyl phosphonates, microwave, alcoholysis, ionic liquid, phosphonic ester-acid, phosphonic acid

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Graphical Abstract

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