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

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-02, Vol.59 (8), p.3063-3068
Main Authors: Bomon, Jeroen, Van Den Broeck, Elias, Bal, Mathias, Liao, Yuhe, Sergeyev, Sergey, Van Speybroeck, Veronique, Sels, Bert F., Maes, Bert U. W.
Format: Article
Language:English
Subjects:
Acids
bond cleavage
C-dealkylation
Catalysts
Catechol
Demethylation
Ferulic acid
green chemistry
Hydroquinone
O-dealkylation
Pyrogallol
renewable resources
Resorcinol
Substrates
Sulfuric acid
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Summary: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 H2SO4) 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. Ferulic acid, a bio‐renewable compound derived from rice bran, has been transformed in catechol, a major commodity chemical, using HCl and water. The protocol is applicable to a variety of other (biorenewable) substrates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201913023