Synthesis of phosphonates from phenylphosphonic acid and its monoesters

Réka Henyecz, Adrienn Kiss, Virág Mórocz, Nóra Zsuzsa Kiss, G. Keglevich

Research output: Contribution to journalArticle

Abstract

Possibilities for the mono- and diesterification of phenylphosphonic acid were evaluated considering the microwave(MW)-assisted direct esterification, and the alkylating esterification. It was found that regarding the monoesterification, the reaction with 15-fold alcohol excess in the presence of [bmim][BF4] additive utilizing MWs is superior than the approach by alkylation. At the same time, for the conversion of the monoester intermediate to the diester, the reaction with alkyl halides in the presence of triethylamine as the base, again under MW irradiation, was found to be the method of choice. Phosphonates with both identical and different alkoxy groups were made available.

Original languageEnglish
Pages (from-to)2642-2650
Number of pages9
JournalSynthetic Communications
Volume49
Issue number20
DOIs
Publication statusPublished - Jan 1 2019

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Organophosphonates
Esterification
Microwave irradiation
Alkylation
Microwaves
Alcohols
phenylphosphonic acid
triethylamine
alkoxyl radical

Keywords

  • Alkylation
  • esterification
  • microwave
  • phosphonate
  • phosphonic acid
  • phosphonic monoester

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of phosphonates from phenylphosphonic acid and its monoesters. / Henyecz, Réka; Kiss, Adrienn; Mórocz, Virág; Kiss, Nóra Zsuzsa; Keglevich, G.

In: Synthetic Communications, Vol. 49, No. 20, 01.01.2019, p. 2642-2650.

Research output: Contribution to journalArticle

Henyecz, Réka ; Kiss, Adrienn ; Mórocz, Virág ; Kiss, Nóra Zsuzsa ; Keglevich, G. / Synthesis of phosphonates from phenylphosphonic acid and its monoesters. In: Synthetic Communications. 2019 ; Vol. 49, No. 20. pp. 2642-2650.
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