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Benzilic acid can be prepared by heating a mixture of benzil, ethanol, and potassium hydroxide. Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde , to benzil , which is transformed to the product by the benzilic acid rearrangement reaction.
The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in 1838, [1] it is the first reported example of a rearrangement ...
Toggle the table of contents. ... A carbanionic 1,2-shift is involved in the benzilic acid rearrangement. ... was the conversion of bis ...
A classic organic reaction of benzil is the benzilic acid rearrangement, in which base catalyses the conversion of benzil to benzilic acid. This reactivity is exploited in the preparation of the drug phenytoin. Benzil also reacts with 1,3-diphenylacetone in an aldol condensation to give tetraphenylcyclopentadienone.
In organic chemistry, the benzoin addition is an addition reaction involving two aldehydes (−CH=O). The reaction generally occurs between aromatic aldehydes or glyoxals (OCH=CHO), [1] [2] and results in formation of an acyloin (−C(O)CH(OH)−). In the classic example, benzaldehyde is converted to benzoin (PhCH(OH)C(O)Ph). [3]
It oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis. Benzyl alcohol is toxic to neonates and is associated with the gasping syndrome.
In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. It is named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978). The method entails treating an acid chlorides with diazomethane. It is a popular method of producing β-amino acids from α-amino acids. [1]
In organic chemistry the Brook rearrangement refers to any [1,n] carbon to oxygen silyl migration. The rearrangement was first observed in the late 1950s by Canadian chemist Adrian Gibbs Brook (1924–2013), after which the reaction is named. [1]