I learned that, a phenol will not react (or react very slowly) with $\ce{PCl5}$ due to its stabilized structure.
How about the $\ce{-OH}$ group on the benzene ring of 4-hydroxybenzoic acid? Will that $\ce{-OH}$ group react with $\ce{PCl5}$? If the answer is yes, is it anything to do with the $\ce{-COOH}$ group?
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