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

Harsági, Nikoletta and Bertha, Csilla and Kiss, Nóra Zsuzsa and Henyecz, Réka and Varga, Petra Regina and Ábrányi-Balogh, Péter and Drahos, László and Keglevich, György (2021) Alcoholysis Versus Fission of the Ester Group During the Reaction of Dialkyl Phenylphosphonates in the Presence of Ionic Liquids. CURRENT ORGANIC CHEMISTRY, 25 (7). pp. 842-848. ISSN 1385-2728

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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.

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