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

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 loadin...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2016-01, Vol.18 (21), p.5839-5844
Main Authors: Jin, Saimeng, Hunt, Andrew J, Clark, James H, McElroy, Con Robert
Format: Article
Language:English
Subjects:
Aliphatic alcohols
Carbonates
Carboxymethylation
Catalysis
Conversion
Dimethyl
Methylation
Phenols
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c6gc01826b