Benzilic Acid Rearrangement converts 1,2- diketone into α hydroxycarboxylic acid in presence of NaOH. For this transformation, 1,2- diketone is first treated with alkali hydroxide to get salt of alpha hydroxy carboxylic acid, which, after an acidic workup, gives α-hydroxy carboxylic acid.
The reaction takes place with both aliphatic and aromatic α-diketones and α-keto aldehydes. Usually diaryl diketones undergo benzilic acid rearrangements in excellent yields, but aliphatic α-diketones that have enolizable α-protons give low yields due to competing aldol condensation reactions.
Under benzilic acid rearrangement reaction conditions Cyclic α-diketones undergo ring-contraction.
When alkoxides or amide anions are used in place of hydroxides, the corresponding esters and amides are formed. This process is called the Benzilic Ester Rearrangement.
Alkoxides that are readily oxidized such as ethoxide (EtO-) or isopropoxide (Me2CHO- ) are not synthetically useful, since these species reduce the α-diketones to the corresponding α-hydroxy ketones. Aryl groups tend to migrate more rapidly than alkyl groups. When two different aryl groups are available, the major product usually results from migration of the aromatic ring with the more powerful electron-withdrawing group(s).
Migratory Aptitude for Benzilic Acid Rearrangement : Aryl groups tend to migrate more rapidly than alkyl groups.
Benzilic acid rearrangement reaction with mechanism:
Here, Benzilic acid rearrangement diphenylmethanol mechanism we will take benzyl as a typical example of the mechanism hydroxide iron attacks on one of the two carbonyl groups to produce a tetrahedral intermediate, which undergoes 1,2 diphenyl migration like this to create a non-isolable species. here, we call this species non-isolable because the alkoxide ion is more basic than the carboxylate ion, so there will be immediate proton transfer to produce the carboxylate ion of benzylic acid, which after protonation during acidic workup will produce benzylic acid.
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My name is Pradip Sanjay W. I’m an organic chemist originally from Maharashtra, India. I have qualified UGC NET-JRF, GATE in chemical sciences and MH-SET exam for assistant professor. I’m currently pursuing my Ph.D. in organic chemistry at the Indian Institute of Technology Hyderabad, India.
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