Principle: In the first step alcohol group of benzoin is oxidized to ketone group forming benzil in presence of concentrated nitric acid. Nitration of aromatic ring is not occurring as sulphuric acid is totally absent in the whole process. Aim: To prepare benzilic acid from benzoin. Step Use: It is used in the manufacture of glycollate pharmaceuticals including clidinium, dilantin, and flutropium. HNO 3.
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Cite this: J. Article Views Altmetric -. Citations 7. PDF KB. Note: In lieu of an abstract, this is the article's first page. Cited By. This article is cited by 7 publications. Benzilic Acid Rearrangement. Archiv der Pharmazie , 4 , Studies on the Fischer indole synthesis: rearrangements of five-, six- and seven-membered cyclic hydrazones of pyrazoline, tetrahydropyridazine and tetrahydro-1,2-diazepine series in polyphosphoric acid.
Verweij, R. Analysis of glycolic acid esters by thin-layer chromatography. Journal of Chromatography A , 69 2 , Justus Liebigs Annalen der Chemie , 1 , Berichte der deutschen chemischen Gesellschaft A and B Series , 56 7 , Berichte der deutschen chemischen Gesellschaft A and B Series , 56 1 , Pair your accounts.
Synthesis of benzilic acid from benzoin
This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in ,  it is the first reported example of a rearrangement reaction. The reaction has been shown to work in aromatic , semi-aromatic, aliphatic , and heterocyclic substrates. The reaction works best when the ketone functional groups have no adjacent enolizable protons, as this allows aldol condensation to compete. The reaction is formally a ring contraction when used on cyclic diketones. It has been found that aryl groups more readily migrate than alkyl groups, and that aryl groups with electron-withdrawing groups migrate the fastest. The reaction is a representative of 1,2-rearrangements.
Benzilic acid rearrangement