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Pentanoyl chloride

Pentanoyl chloride is an acyl chloride derived from pentanoic acid. It is a colorless liquid that is used to attach the valeroyl group. It is usually produced by chlorination of valeric acid.

Reactions

Like related acyl chlorides, valeroyl chloride hydrolyzes readily:

CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>C(O)Cl + H<sub>2</sub>O → CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CO<sub>2</sub>H + HCl

Alcohols react to give esters:

CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>C(O)Cl + ROH → CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CO<sub>2</sub>R + HCl

Amines react to give amides:

CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>C(O)Cl + R<sub>2</sub>NH → CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>C(O)NR<sub>2</sub> + HCl

Benzene reacts under conditions of the Friedel-Crafts reaction to give valerophenone:

CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>C(O)Cl + C<sub>6</sub>H<sub>6</sub> → CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>C(O)C<sub>6</sub>H<sub>5</sub> + HCl

References