ORGLIST: Use of phosphorus pentachloride in acid chloride synthesis

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From: cardman (cardman400$##$
Date: Mon Oct 24 2005 - 21:04:39 EDT

Does anyone have any tips on the use of PCl5 ? I tried
using a 1:1 molar ratio of pentachloride and
4-azidobenzoic acid in refluxing benzene and got a
yield of only 50% of the acid chloride. Of course I
thought about using a large excess of chloride to
drive the rxn forward, but then how do I separate off
the xs? I want to carry out an esterification, so I
can't just use the reaction mixture as it is (or can

Actually, the same thing happened with oxalyl
chloride: I recrystallized the residue, and a
significant portion of the unreacted acid crystallized
out first.

I can't use thionyl chloride because my company has to
first apply for a permit. Apparently thionyl chloride
is on the DEA's list of restricted chemicals.

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