So it´s benzylchloride what you are after - what about an alternative starting compound? Toluene either direct (not so clean of course) or by toluene to benzylalcohol? (I guess you might store this compound for later use as you prefer to synth some easy & clean to process legal precursors first - a good concept IMHO)
Benzoic acid is also a good start here - benzene is for sure the last favorable compound - cancerogen, seen as suspicious (somehow), and a Friedl-Craffts is a whole lot more a mess as even the Loomis (tol.->BzCl, by hypochlorits).
If you want to go the hard way by all means I have to say: Chloromethylation is for the weak. Fischer-Tropsch is for real men.
Yes and.....
.....Bz-alcohol is de facto OTC as solvent/cleaner in motoristic and as thinner for two component epoxides. Two quick examples and thats unsporty, agreed.