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Issue 10, 2005
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Water-solvent method for tosylation and mesylation of primary alcohols promoted by KOH and catalytic amines

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Abstract

We have developed an efficient water-solvent method for p-toluenesulfonylation (tosylation) and methanesulfonylation (mesylation) of primary alcohols using p-toluenesulfonyl chloride and methanesulfonyl chloride, respectively, promoted by KOH and catalytic amines. The reaction was performed by maintaining the pH at around 10 using a pH controller to prevent the undesirable decomposition of sulfonyl chlorides. Several primary alcohols were smoothly sulfonylated in excellent yield. The choice of the amine catalyst (0.1 equiv.) was important: N,N-dimethylbenzylamine, a sterically unhindered and lipophilic tertiary amine, was effective for the tosylation, whereas N,N-dimethylbutylamine and triethylamine were effective for the mesylation. The present Schotten–Baumann-type method is the first example of catalytic sulfonylation using sulfonyl chlorides, and is a green chemical process due to the use of water as the solvent.

Graphical abstract: Water-solvent method for tosylation and mesylation of primary alcohols promoted by KOH and catalytic amines

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Publication details

The article was received on 15 Apr 2005, accepted on 11 Aug 2005 and first published on 26 Aug 2005


Article type: Paper
DOI: 10.1039/B505345E
Citation: Green Chem., 2005,7, 711-715
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    Water-solvent method for tosylation and mesylation of primary alcohols promoted by KOH and catalytic amines

    J. Morita, H. Nakatsuji, T. Misaki and Y. Tanabe, Green Chem., 2005, 7, 711
    DOI: 10.1039/B505345E

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