# Reaction mechanism with benzylchloride (KMnO4 and Soda lime)

So I know that $$\ce{KMnO4}$$ converts any side chain irrespective of chain length to -$$\ce{COOH}$$ group and Soda lime converts that into the respective alkane. But in benzyl chloride, the alkyl group side chain also has a chlorine atom attached. How would the mechanism proceed?

It is given that Benzene is the product.

• You have water present, benzyl chloride is a reactive species. Consider the possibility that the benzyl chloride hydrolyses to benzyl alcohol early in the reaction Oct 23, 2019 at 15:56
• @Waylander Ok, but then how would KMnO4 react with a side chain containing alcohol? Oct 23, 2019 at 16:00
• Alcohol to acid is a std permangate oxidation Oct 23, 2019 at 16:37
• @Waylander Ah i haven't gotten to that part i guess Oct 23, 2019 at 16:39

As @Waylander's comment elsewhere, benzyl chloride might have converted to benzyl alcohol before get oxidized to benzoic acid in acidic $$\ce{KMnO4}$$ solution (the first step). This oxidation is well known (see here). The second step is heating (may be $$\gt \pu{200 ^\circ C}$$) of solid benzoic acid in the presence of solid soda lime to cause the decarboxylation. This reaction is well described by Dr. Jim Clark (here) and also here.