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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 (CC BY 3.0).

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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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