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

Saimeng Jin; Andrew J. Hunt; James H. Clark; Con Robert McElroy

doi:10.1039/C6GC01826B

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

Saimeng Jin, Andrew J. Hunt, James H. Clark, Con Robert McElroy

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	5839-5844
Number of pages	6
Journal	Green Chemistry
Volume	18
Issue number	21
Early online date	18 Aug 2016
DOIs	https://doi.org/10.1039/C6GC01826B https://doi.org/10.1039/c6gc01826b
Publication status	Published - 18 Aug 2016

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

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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AU - Clark, James H.

AU - McElroy, Con Robert

N1 - © 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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AB - 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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Acid-catalysed carboxymethylation, methylation and dehydration of alcohols and phenols with dimethyl carbonate under mild conditions

Abstract

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