ORGLIST: hydroxyl benzylation in the presance of carboxyllic acid

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From: ohad ilovich (ilovich$##$pob.huji.ac.il)
Date: Wed Nov 02 2005 - 04:57:54 EST


Hello everybody,

I would like to perform the direct benzilation of a hydroxyl on a =
molecule containing a carboxylic acid.
I've seen many reaction in which benzyl bromide benzylated acids in the =
presence of different bases.
I've also seen a reaction with benzyl chloride and aqueous NaOH be very =
selective towards the hydroxyl (76% yield)
so:
is benzyl bromide no useful to me with it being so reactive?
is there a better way to do this than I found? (except protecting the =
acid beforehand as an ester)
why is the second method so selective towards the hydroxyl?

thanks
Ohad


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