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Issue 63, 2016
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Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

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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.

Graphical abstract: Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

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Publication details

The article was received on 16 Apr 2016, accepted on 10 Jun 2016 and first published on 10 Jun 2016


Article type: Paper
DOI: 10.1039/C6RA09841J
RSC Adv., 2016,6, 58443-58451

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    Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

    M. Y. Lui, K. S. Lokare, E. Hemming, J. N. G. Stanley, A. Perosa, M. Selva, A. F. Masters and T. Maschmeyer, RSC Adv., 2016, 6, 58443
    DOI: 10.1039/C6RA09841J

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