Chemoselective and scalable preparation of alkyl tosylates under solvent-free conditions

The improved method for the efficient tosylation of alcohols has been reported using two procedures (A and B). Procedure A: methanol, ethanol, benzyl alcohols, and valuable ethylene glycols can be converted into their corresponding alkyl tosylates in very fast, simple, and efficient grinding method...

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Bibliographic Details
Published in:Tetrahedron 2007-06, Vol.63 (23), p.5083-5087
Main Authors: Kazemi, Foad, Massah, Ahmad R., Javaherian, Mohammad
Format: Article
Language:English
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Summary:The improved method for the efficient tosylation of alcohols has been reported using two procedures (A and B). Procedure A: methanol, ethanol, benzyl alcohols, and valuable ethylene glycols can be converted into their corresponding alkyl tosylates in very fast, simple, and efficient grinding method using potassium carbonate as solid base. Other primary and secondary alcohols need to add potassium hydroxide to reaction mixture (procedure B). High selectivity of tosylation was observed for these two procedures. Scale up ability was found in this method even in 100 mmol of substrate. The present method is the example of solid-state tosylation using tosyl chloride, and is a green chemical process due to solvent-free conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.03.083