Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

Matthew Y. Lui, Kapil S. Lokare, Ellen Hemming, Jessica N.G. Stanley, Alvise Perosa, Maurizio Selva, Anthony F. Masters, Thomas Maschmeyer*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Using a focused microwave reactor, methylation with dimethyl carbonate (DMC) of 1,2- and 1,4-dihydroxybenzene derivatives, found in the product spectrum of lignin depolymerisation, leads to the respective aromatic bis-methyl ethers with excellent isolated yields. Stoichiometric as well as catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective for the bis-methylation of these dihydroxybenzenes at relatively mild temperatures (160-190 °C). Conversion of resorcinol (1,3-dihydroxybenzene) under similar conditions leads to a mixture of 1,3-dimethoxybenzene and methyl 2,4-dimethoxybenzoate. The unusual reactivity of resorcinol's phenyl ring towards DMC can be explained by the synergic effect of its two strongly activating ortho/para directing groups.

Original languageEnglish
Pages (from-to)58443-58451
Number of pages9
JournalRSC Advances
Volume6
Issue number63
DOIs
Publication statusE-pub ahead of print - Jun 2016

Scopus Subject Areas

  • Chemistry(all)
  • Chemical Engineering(all)

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