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

Molecules

Rui Ding¹  Yong He¹  Xiao Wang¹  Jingli Xu¹  Yurong Chen¹  Man Feng¹ 

[1]Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, China

关键词: tosyl chloride;    chlorination;    tosylation;    benzyl alcohols;    pyridine methanols;   

DOI  :  10.3390/molecules16075665

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.