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Acid-catalysed carboxymethylation, methylation and dehydration of alcohols and phenols with dimethyl carbonate under mild conditions

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JournalGreen Chemistry
DateAccepted/In press - 18 Aug 2016
DateE-pub ahead of print - 18 Aug 2016
DatePublished (current) - 18 Aug 2016
Issue number21
Volume18
Number of pages6
Pages (from-to)5839-5844
Early online date18/08/16
Original languageEnglish

Abstract

Dimethyl carbonate (DMC) chemistry has been extended to include acid-catalysed reactions of different aliphatic alcohols and phenols. For the first time, p-toluenesulfonic acid (PTSA), H2SO4, AlCl3 and FeCl3 have been shown to aid carboxymethylation for primary aliphatic alcohols at catalytic loadings with quantitative conversion and selectivity. For carboxymethylation of secondary alcohols, stoichiometric PTSA and catalytic AlCl3 both gave quantitative conversion and selectivity. Stoichiometric FeCl3 and H2SO4 promoted dehydration of linear aliphatic alcohols. Additionally FeCl3 catalysed methylation of cyclohexanol, whilst AlCl3 resulted in methylation of phenolic compounds. This research expands the range of potential application for DMC in green chemistry.

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© The Royal Society of Chemistry 2016. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

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