title: Treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates.
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.
authors: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, China. dingrui@mail.bnu.edu.cn
authors: Rui
authors: R
authors: Ding
authors: Yong
authors: Y
authors: He
authors: Xiao
authors: X
authors: Wang
authors: Jingli
authors: J
authors: Xu
authors: Yurong
authors: Y
authors: Chen
authors: Man
authors: M
authors: Feng
authors: Chuanmin
authors: C
authors: Qi
mesh_terms: D001592:Benzyl Alcohols / Q000737:chemistry; D054879:Halogenation; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D001592:Benzyl Alcohols; D014105:Tosyl Compounds; C025506:4-toluenesulfonyl chloride; D000432:Methanol