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, György Keglevich*

Journal Name: Current Organic Chemistry

Volume 25 , Issue 7 , 2021


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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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Article Details

VOLUME: 25
ISSUE: 7
Year: 2021
Published on: 11 February, 2021
Page: [842 - 848]
Pages: 7
DOI: 10.2174/1385272825666210212115649

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