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

5 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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