Synthesis of Chalcones: An Improved High-Yield and Substituent-Independent Protocol for an Old Structure

Ana Donaire-Arias, Martin L. Poulsen, Jaime Ramón-Costa, Ana Maria Montagut, Roger Estrada-Tejedor, José I. Borrell

Research output: Indexed journal article Articlepeer-review

Abstract

Chalcones are a type of molecule that can be considered as easily synthesizable through aldol condensation or that can be readily purchased from habitual commercial vendors. However, on reviewing the literature, one realizes that there are no standard procedures for such aldol condensations, that there exists a wide range of alternative methods for the aldol condensation (indicating that such a condensation is not always simple), and that, in many cases, low yields are obtained that involve purifications by recrystallization or column chromatography. To develop a robust standard protocol independent of the nature of the substituents present on the acetophenone or the benzaldehyde involved in the aldol condensation leading to the chalcone, we made a comparison between an aldol condensation in KOH/EtOH and a Wittig reaction between the corresponding ylide and benzaldehyde in water. We describe an improved procedure for the Wittig reaction and a protocol for the elimination of the Ph3P=O byproduct (and the excess of ylide used) by filtration of the crude reaction product through a silica gel plug. We thus demonstrate that such an improved procedure can be a general method for the synthesis of chalcones in high yield and excellent purity and is clearly an improvement on the classical aldol condensation.

Original languageEnglish
Article number7576
JournalMolecules
Volume28
Issue number22
DOIs
Publication statusPublished - Nov 2023

Keywords

  • aldol condensation
  • chalcones
  • Wittig reaction

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