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benzyl chloride : ウィキペディア英語版
benzyl chloride

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Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colourless liquid is a reactive organochlorine compound that is a widely used chemical building block.
==Preparation==
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine:〔M. Rossberg et al. "Chlorinated Hydrocarbons" in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. 〕
:C6H5CH3 + Cl2 → C6H5CH2Cl + HCl
In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds via free radical, involving the intermediacy of the chlorine atoms.〔.〕 Side products of the reaction include benzal chloride and benzotrichloride.
Other methods exist, such as the Blanc chloromethylation of benzene. Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid.

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