[MətHylFrÆtH]

I was wondering if there is any such thing as an oxidizing agent that will oxidize primary alcohols and/or aldehydes to carboxylic acids but will not oxidize the benzylic carbon to a ketone.


I was wondering how to do this because of a synthesis that involves an intramolecular Freidel Crafts Acylation, for which a carboxylic acid is needed to form the acid chloride

For example I think using CrO₃/ H⁺/H₂O (Jones) on 4-phenyl butanol will give 4-phenyl-4-oxo-butanoic acid instead of 4-phenyl-butanoic acid which is my desired intermediate.

[TheUnassuming]

Indeed there are.  Most won't oxidize a benzyl carbon.
A good starting point for you will be the wiki page:
http://en.wikipedia.org/wiki/Alcohol_oxidation

In my experience, Jones conditions won't oxidize a benzyl carbon.  Jones also tends to give the cleanest crude and best yield of the alcohol to acid oxidation's. 

[MətHylFrÆtH]

oh rly?

well that goes contrary what was suggested to me by Vollhardt 6th which is the organic chemistry textbook that I use....assuming I read it right.


Does anyone have experience carrying out a reaction that is similar to the one I have described?

[AlphaScent]

I am soon going to run this reaction.  I have never run this catalytic version, but the stoichiometric method(s) give the nasty chromium salts.

I have the paper.

PM me if you would like it.  It is a PDF and the forum doesnt look kindly on PDFs as attachments.


Cheers!

[TheUnassuming]

You read it right, it just glosses over the speed of the relative reactions and I should have been more clear/exact with my words.  You can oxidize benz carbons with various oxidants but you have to hit it much harder than you do to oxidize an alcohol.  To oxidize your alchohol with Jones conditions you will be running at -10 to 0 ºC for about 30min.  To oxidize your carbon you will need to heat it for an extended period of time. 
I have run this reaction many times on a variety of substrates with great success unless my compound turns out to be unstable to the strongly acidic conditions.  A good quick guide can be found on notvoodoo.  Chromium salts are poisonous, so show them the respect they deserve and you won't have any problems.