Question

How to get toluene from benzyl alcohol

Answer 1

Here is a nice article, which describes the kinetics of toluene oxidation supporting Kyle's answer above.  However, it appears that benzyl alcohol is not only a theoretical but also a real minor product in the practice (in the plant). Then of course a small amount of benzylbenzoate can also be present. Otherwise, Kyle is absolutely right. Oxidation of toluene, like that of many other C-H-s is a descending road from the hill by thermodynamics, i.e. the secondary products are oxidized easier than primaries and the most favored is stopping below (i.e. CO2). Although, the oxidation of toluene goes partly through benzyl alcohol for the above mentioned reason it is better to use benzoic acid, benzaldehyde, benzyl chloride, bromobenzene etc. with the appropriate one step synthetic route to prepare benzyl alcohol if that is your only goal.