Brønsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol

Jeroen Bomon; Elias Van Den Broeck; Mathias Bal; Yuhe Liao; Sergey Sergeyev; Veronique Van Speybroeck; Bert F Sels; Bert U W Maes

doi:10.1002/anie.201913023

Brønsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol

Angew Chem Int Ed Engl. 2020 Feb 17;59(8):3063-3068. doi: 10.1002/anie.201913023. Epub 2020 Jan 21.

Authors

Jeroen Bomon¹, Elias Van Den Broeck², Mathias Bal¹, Yuhe Liao³, Sergey Sergeyev¹, Veronique Van Speybroeck², Bert F Sels³, Bert U W Maes¹

Affiliations

¹ Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerp, Belgium.
² Center for Molecular Modeling, Ghent University, Technologiepark 46, 9052, Zwijnaarde, Belgium.
³ Center for Sustainable Catalysis and Engineering, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.

PMID: 31765514
DOI: 10.1002/anie.201913023

Abstract

An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C-O (demethylation) and C-C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H₂ SO₄ ) as catalyst in pressurized hot water (250 °C, 50 bar N₂ ). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.

Keywords: C-dealkylation; O-dealkylation; bond cleavage; green chemistry; renewable resources.

Publication types

Research Support, Non-U.S. Gov't