Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates

Shih Chieh Kao, Yi Ching Lin, Ilhyong Ryu, Yen-Ku Wu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    6 Scopus citations

    Abstract

    Described is a tetrabutylammonium fluoride-mediated hydroxyalkylation reaction of phenols with cyclic carbonates. This operationally simple method enables the synthesis of a variety of aryl β-hydroxyethyl ethers in good to excellent yields with a very small amount of catalyst loading (0.1–1 mol%). Of particular note is the efficient conversion of aromatic diols and phloroglucinol to the corresponding bis- and tris-hydroxyethylated products. To further showcase the versatility of this protocol, guaifenesin was prepared with a single step by the condensation of guaiacol and glycerol carbonate. We also developed a flow ethoxylation process permitting the continuous synthesis of multiflorol. (Figure presented.).

    Original languageEnglish
    Pages (from-to)3639-3644
    Number of pages6
    JournalAdvanced Synthesis and Catalysis
    Volume361
    Issue number15
    DOIs
    StatePublished - 5 Aug 2019

    Keywords

    • 2-phenoxyethanol
    • TBAF
    • ethoxylation
    • ethylene carbonate
    • flow chemistry
    • phenols

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