4.8 Article

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

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 8, 页码 3063-3068

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913023

关键词

green chemistry; O-dealkylation; C-dealkylation; renewable resources; bond cleavage

资金

  1. Research Foundation Flanders (FWO) (WOG)
  2. Research Foundation Flanders (FWO) (BioFact Excellence of Science project) [30902231]
  3. UAntwerp (BOF)
  4. Research Board of UGent
  5. VLAIO/Catalisti (ARBOREF)
  6. BIO-HarT project
  7. Hercules
  8. Francqui Foundation
  9. FWO

向作者/读者索取更多资源

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 degrees 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.

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