Halogenated hydrocarbons benzyl chloride

The presence of a halogen atom in the side chain greatly facilitates the oxidation, so that substances such as benzyl chloride or benzyl alcohol are much more easily oxidized than are the corresponding hydrocarbons ... 

A survey of the chlotomethylation of aromatic compounds has been made, and a thorough study of the conditions of the reaction for the production of benzyl chloride has been carried out. The reaction is generally applicable to aromatic hydrocarbons. The effect of substituents on the ease of chloromethylation is pronounced alkyl and alkoxyl groups facilitate the introduction of the chloromethyl group, whereas halogen, Carboxyl, and nitro substituents retard or prevent the reaction. Zinc chloride, sulfuric acid, and phosphoric acid have been used as catalysts when needed. A chief by-product is the f is -chloromethyl compound. 

Halogenation of hydrocarbons. Walling found /-butyl hypochlorite useful for light- or radical-induced chain chlorination of toluene. Thus, in the presence of azobisisobutyronitrile as initiator, the reaction with toluene at 40° affords benzyl chloride (84%), /-butanol (97%), and 1-3% each of chlorololuenes, methyl chloride, and acetone. 

BENZYL CHLORIDE. C.HyCHiCI. High purity aluminum was resistant to benzyl chloride in laboratory tests at ambient temperature. Benzyl chloride caused corrosion of other alloys, increasing as temperature increased. CAUTION See Halogenated Hydrocarbons." See also Ref (2) p. 100, (3) p. Ill, (7)p.33. 

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