Reaction of salicylic acid with PCl5 [duplicate]








**This question already has an answer here**:
 
 




[Can the hydroxyl group of 4-hydroxybenzoic acid react with phosphorus pentachloride?](/questions/35359/can-the-hydroxyl-group-of-4-hydroxybenzoic-acid-react-with-phosphorus-pentachlor)

 (1 answer)
 

Closed 7 years ago.



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


![substrate](https://i.stack.imgur.com/LNA2E.jpg)


According to me the product should be:


![alternative product](https://i.stack.imgur.com/5y9DU.jpg)


But why the product is supposed to be:


![product](https://i.stack.imgur.com/tvkk4.jpg)




Photo shows PCl**3** on the photo - not PCl**5**.


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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