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Molecules 2011, 16(7), 5665-5673; doi:10.3390/molecules16075665
Article

Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates

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Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, China
* Author to whom correspondence should be addressed.
Received: 5 April 2011 / Accepted: 13 June 2011 / Published: 1 July 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.
Keywords: tosyl chloride; chlorination; tosylation; benzyl alcohols; pyridine methanols tosyl chloride; chlorination; tosylation; benzyl alcohols; pyridine methanols
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Ding, R.; He, Y.; Wang, X.; Xu, J.; Chen, Y.; Feng, M.; Qi, C. Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates. Molecules 2011, 16, 5665-5673.

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