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13.14: Carboxylic Acids to Acid Chlorides

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JoVE Core
Organic Chemistry

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Carboxylic Acids to Acid Chlorides
 
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13.14: Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.

Figure1

An alternative reagent for converting a carboxylic acid to an acid chloride is phosphorus pentachloride. The mechanism involves the attack by a carboxylic acid at the phosphorus center of PCl5 while eliminating a chloride ion. Subsequently, the attack by this chloride ion at the carbonyl center results in an acid chloride, along with the formation of phosphorus oxychloride. The formation of a highly stable P=O bond drives the reaction forward.

Figure2

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Keywords: Carboxylic Acids Acid Chlorides SOCl2 PCl5 Friedel-Crafts Acylation Phosphorus Pentachloride Mechanism Carbonyl Phosphorus Oxychloride

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