Facile Synthesis of 4-Hydroxycinnamaldehydes

Yimin Zhu, Allison Mohammadi, John Ralph

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

4-Hydroxycinnamaldehydes are key intermediates in the biosynthesis and degradation of lignins, the class of aromatic polymers that are responsible for much of the recalcitrance in converting lignocellulosic biomass to liquid fuels. Access to these aldehydes is needed for investigation of biochemical pathways, a crucial step in manipulating lignin biosynthesis for cost-effective biofuels production. Here, p-coumaraldehyde, caffealdehyde, coniferaldehyde, and sinapaldehyde were efficiently prepared by coupling the corresponding 4-hydroxycinnamic acids with N,O-dimethylhydroxylamine, followed by selective reduction with diisobutylaluminum hydride. The protecting-group-free total synthesis of these aldehydes does not require the use of a controlled atmosphere, nor chromatographic purification; thus, although it remains in the realm of moderately well-trained synthetic chemists, the syntheses are particularly convenient.

Original languageEnglish (US)
Pages (from-to)407-411
Number of pages5
JournalBioenergy Research
Volume5
Issue number2
DOIs
StatePublished - Jun 2012

All Science Journal Classification (ASJC) codes

  • Renewable Energy, Sustainability and the Environment
  • Agronomy and Crop Science
  • Energy (miscellaneous)

Fingerprint Dive into the research topics of 'Facile Synthesis of 4-Hydroxycinnamaldehydes'. Together they form a unique fingerprint.

Cite this