What it is the product when salicylic acid (2-hydroxybenzoic acid) is reacted with $\ce{PCl5}$?


According to me the product should be:

alternative product

But why the product is supposed to be:



Photo shows PCl3 on the photo - not PCl5.

You have two potentially reactive groups. Phenol (with OH) and carboxylic acid to consider. carboxylic acid turns into chloro anhydride just as both pictures show. Now alcohols react with PCl3, but phenols don't. YOu have a phenol, so it will not react, so the corect answer is (B).

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  • $\begingroup$ Why phenol will not react $\endgroup$ – Koolman Jul 21 '16 at 14:26
  • $\begingroup$ @koolman, look at the posts linked in the comments below. They answer that question in quite some detail. $\endgroup$ – NotEvans. Jul 21 '16 at 16:38

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