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Benzoic anhydride

Benzoic anhydride is the organic compound with the formula (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O. It is the acid anhydride of benzoic acid and the simplest symmetrical aromatic acid anhydride. It is a white solid.

Preparation and reactions

It is usually prepared by the dehydration reaction of benzoic acid, e.g. using acetic anhydride:

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

Alternatively, sodium benzoate can be treated with benzoyl chloride. It can be produced by dehydrating benzoic acid by heating.

Benzoic anhydride provides a convenient way to prepare benzoic esters:

(C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O + ROH → C<sub>6</sub>H<sub>5</sub>CO<sub>2</sub>H + C<sub>6</sub>H<sub>5</sub>CO<sub>2</sub>R

References