Editing Benzoic acid (section)

== Reactions ==

Reactions of benzoic acid can occur at either the [[aromaticity|aromatic ring]] or at the [[carboxyl group]].
===Aromatic ring===
:[[Image:Benzoic acid-chemical-reaction-1.svg|class=skin-invert-image|center|benzoic acid aromatic ring reactions]]

[[Electrophilic aromatic substitution]] reaction will take place mainly in 3-position due to the [[deactivating group|electron-withdrawing]] [[carboxylic group]]; i.e. benzoic acid is [[electrophilic aromatic substitution#Meta directors|''meta'' directing]].<ref>{{OrgSynth | author=Brewster, R. Q. |author2=Williams, B. |author3=Phillips, R. |title=3,5-Dinitrobenzoic Acid| | collvol = 3 | collvolpages = 337 | year= 1955 | prep = cv3p0337}}</ref>

=== Carboxyl group ===
Reactions typical for [[carboxylic acid]]s apply also to benzoic acid.<ref name=Ull/>

* Benzoate [[ester]]s are the product of the acid catalysed reaction with [[Alcohol (chemistry)|alcohol]]s.
* Benzoic acid [[amide]]s are usually prepared from [[benzoyl chloride]].
* Dehydration to [[benzoic anhydride]] is induced with [[acetic anhydride]] or [[phosphorus pentoxide]].
* Highly reactive acid derivatives such as [[Acyl halide|acid halides]] are easily obtained by mixing with [[halogenation]] agents like [[phosphorus chlorides]] or [[thionyl chloride]].
* [[Orthoester]]s can be obtained by the reaction of alcohols under acidic water free conditions with [[benzonitrile]].
* Reduction to [[benzaldehyde]] and [[benzyl alcohol]] is possible using [[DIBAL-H]], [[lithium aluminium hydride|LiAlH<sub>4</sub>]] or [[sodium borohydride]].
* [[Decarboxylation]] to benzene may be effected by heating in [[quinoline]] in the presence of copper salts.  [[Hunsdiecker decarboxylation]] can be achieved by heating the silver salt.
:[[Image:Benzoic acid-chemical-reaction-2.svg|class=skin-invert-image|center|400px|benzoic acid group reactions]]