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Issue 1, 2008
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The methylation of benzyl-type alcohols with dimethyl carbonate in the presence of Y- and X-faujasites: selective synthesis of methyl ethers

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Abstract

At 165–200 °C, in the presence of sodium-exchanged faujasites (NaX or NaY) as catalysts, the reaction of dimethyl carbonate with benzyl-, o- and p-methoxybenzyl-, p-hydroxybenzyl-, diphenylmethyl-, and triphenylmethyl-alcohols (1a, 2a,b, 3a, 4a, and 4c, respectively), produces the corresponding methyl ethers in up to 98% yields. A peculiar chemoselectivity is observed for hydroxybenzyl alcohols (compounds 3a and 3b, para- and ortho-isomers) whose etherification takes place without affecting the OH aromatic groups. Acid–base interactions of alcohols and DMC over the faujasite surface offer a plausible explanation for the catalytic effect of zeolites NaY and NaX, as well as for the trend of reactivity shown by the different alcohols (primary > secondary > tertiary). However, in the case of substrates with mobile protons in the β-position (i.e.1-phenylethanol and 1,1-diphenylethanol), the dehydration reaction to olefins is the major, if not the exclusive, process.

Graphical abstract: The methylation of benzyl-type alcohols with dimethyl carbonate in the presence of Y- and X-faujasites: selective synthesis of methyl ethers

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Article information


Submitted
23 May 2007
Accepted
18 Oct 2007
First published
09 Nov 2007

Green Chem., 2008,10, 73-79
Article type
Paper

The methylation of benzyl-type alcohols with dimethyl carbonate in the presence of Y- and X-faujasites: selective synthesis of methyl ethers

M. Selva, E. Militello and M. Fabris, Green Chem., 2008, 10, 73
DOI: 10.1039/B707774B

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