benzyl alcohol from benzene

[El_Zorro]

Does anyone know of a synth of benzyl alcohol from benzene?  I've UTFSE, and I've looked at Rhod's site, and I've searched through the Organic Synthesis site that's linked from Rhod's page, and I couldn't find anything for benzyl alcohol going straight from benzene.  Can anyone help me out here?

[hest]

Chloromethylation ? Aldhydeformation with DMF ? Grignard to the acid? methylation and nbs-bromination ?

[El_Zorro]

Well, what I want to get is benzyl chloride, but my thoughts are that the chloromethylation synths might be a little low yielding.  But the synth of benzyl chloride from benzyl alcohol is easy, clean, and high yielding.  So I was just hoping that there would be a high-yeilding synth of benzyl alcohol from benzene that involved one step.  I haven't found anything, apparently no one but me wants to make it, so they just buy it.

[Rhodium]

There are no simple, one-step syntheses of benzyl alcohol from benzene, the only thing I found by a quick literature search was Rh-catalyzed carbonylation of benzene under uv irradiation in an atmosphere of carbon monoxide, where benzaldehyde, benzyl alcohol and biphenyl could be isolated from the reaction mixture...

[El_Zorro]

Dammit.  I guess I gotta go through the trouble of chloromethylation.

[lugh]

Benzyl alcohol is usually made industrially from benzyl chloride    Thus the most facile route for converting benzene to benzyl alcohol would be chlormethylation to benzyl chloride, followed by reaction with potasium/sodium carbonate, see

Patent DE484662

for details  

[El_Zorro]

Lol, great, I was starting to think it couldn't be done.

Fuck.  I was looking for a goddman synth that gives a 90%+ yield going from benzene to benzyl chloride.  I guess it was just too much to ask.

[ragnaroekk]

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.

[El_Zorro]

Yeah, I realize that there are more favorable starting materials to get benzyl chloride from.  But the only problem is, I'm not looking for just plain old benzyl chloride, I'm looking for a substituted benzyl chloride, and I just don't have access to any substituted toluenes or benzoic acids, at least the ones that I want.

[urushibara]

yeah, I understand that toluene can be transformed into benzyl alcohol by running the vapours over a catalyst at 300 degrees C, also I think benzaldehyde can be formed in this reaction (rats) anyway, I'm fairly sure it's on rhodium's site.