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Brønsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio‐Catechol
Author(s) -
Bomon Jeroen,
Van Den Broeck Elias,
Bal Mathias,
Liao Yuhe,
Sergeyev Sergey,
Van Speybroeck Veronique,
Sels Bert F.,
Maes Bert U. W.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913023
Subject(s) - ferulic acid , pyrogallol , catechol , chemistry , demethylation , hydroquinone , catalysis , organic chemistry , bond cleavage , catechol o methyl transferase , biochemistry , gene expression , dna methylation , gene , allele
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 H 2 SO 4 ) as catalyst in pressurized hot water (250 °C, 50 bar N 2 ). 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.