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Étard reaction : ウィキペディア英語版
Étard reaction

The Étard reaction is a chemical reaction that involves the direct oxidation of an aromatic or heterocyclic bound methyl group to an aldehyde using chromyl chloride.〔

〕〔
〕 It is named for the French chemist Alexandre Léon Étard (5 January 1852, Alençon – 1 May 1910). For example, toluene can be oxidized to benzaldehyde:
== Reaction Mechanism ==
The reaction mechanism proceeds via an ene reaction with chromyl chloride, forming the precipitated Étard complex. The Étard complex is then decomposed by a () sigmatropic rearrangement under reducing conditions to prevent further oxidation to a carboxylic acid. Reducing conditions for the decomposition of the Étard complex are provided by saturated aqueous sodium sulphite. Typical solvents for the reaction include carbon disulfide, chloroform, and carbon tetrachloride, with carbon tetrachloride being the most common. To obtain a highly purified aldehyde product, the Étard complex precipitate is often purified before decomposition in order to prevent reaction with any unreacted reagent. The reaction is normally carried out for a few days to several weeks and the yields are high.

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