Gram-scale economical synthesis of trans-coniferyl alcohol and its corresponding thiol

Hassan Amer, Vebi Mimini, Dominik Schild, Uwe Rinner, Markus Bacher, Antje Potthast, Thomas Rosenau

    Research output: Contribution to journalArticleScientificpeer-review

    Abstract

    Coniferyl alcohol is considered to be a potent antioxidant and a precursor of several bioactive products. In addition, it is a frequently used as a model compound in lignin chemistry. Coniferyl thiol is used analogously to study the sulfur chemistry in technical lignins. Coniferyl alcohol was synthesized in a large scale from commercially available ferulic acid by a mixed anhydride reduction method which affords high yields (84%) under very mild conditions and allows using sodium borohydride. The nucleophilic substitution of 4-O-acetylated coniferyl alcohol (3) with thioacetic acid in the presence of dimethylformamide (DMF) dineopentylacetal afforded 4-O-acetylated coniferyl thioacetate (5) in a 70% yield, which, in a 72% yield, was deprotected to the respective thiol (6). Both coniferyl alcohol and coniferyl thiol were comprehensively analytically characterized [one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopy]. The presented approach renders the two model substances readily available on a gram scale and according to low-risk, environmentally compatible protocols.

    Original languageUndefined/Unknown
    Pages (from-to)197–202
    JournalHolzforschung
    Volume74
    Issue number2
    DOIs
    Publication statusPublished - 2020
    MoE publication typeA1 Journal article-refereed

    Keywords

    • coniferyl alcohol
    • coniferyl thiol
    • technical lignin

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