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Benzyl is most commonly abbreviated Bn. For example, benzyl alcohol can be represented as BnOH. Less common abbreviations are Bzl and Bz, the latter of which is ambiguous as it is also the standard abbreviation for the benzoyl group C 6 H 5 C(O)−. Likewise, benzyl should not be confused with the phenyl group C 6 H 5 −, abbreviated Ph.
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 reaction. [2] It has become a classic reaction in organic synthesis and has been reviewed many times before.
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.
Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol. [ 13 ] Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and anti-fungal properties.
The Sommelet–Hauser rearrangement (named after M. Sommelet [1] and Charles R. Hauser [2]) is a rearrangement reaction of certain benzyl quaternary ammonium salts. [3] [4] The reagent is sodium amide or another alkali metal amide and the reaction product a N,N-dialkylbenzylamine with a new alkyl group in the aromatic ortho position.
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. [ 2 ] Uses
The benzyl alcohol thus formed is quickly converted to the chloride under the reaction conditions. Mechanism of Blanc chloromethylation Other possibilities for the electrophile include (chloromethyl)oxonium cation (ClH 2 C–OH 2 + ) or chlorocarbenium cation (ClCH 2 + ), which may be formed in the presence of zinc chloride. [ 4 ]
The Sommelet reaction is an organic reaction in which a benzyl halide is converted to an aldehyde by action of hexamine and water. [1] [2] It is named after the French chemist Marcel Sommelet, who first reported the reaction in 1913. [3] One example, thiophene-2-carboxaldehyde is prepared by the reaction of hexamine with 2-chloromethylthiophene ...