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Cannizzaro first accomplished this transformation in 1853, when he obtained benzyl alcohol and potassium benzoate from the treatment of benzaldehyde with potash (potassium carbonate). More typically, the reaction would be conducted with sodium hydroxide or potassium hydroxide , giving the sodium or potassium carboxylate salt of the carboxylic ...
Benzaldehyde is easily oxidized to benzoic acid in air at room temperature, [15] causing a common impurity in laboratory samples. Since the boiling point of benzoic acid is much higher than that of benzaldehyde, it may be purified by distillation. Benzyl alcohol can be formed from benzaldehyde by means of hydrogenation.
Benzyl alcohol is produced industrially from toluene via benzyl chloride, which is hydrolyzed: . C 6 H 5 CH 2 Cl + H 2 O → C 6 H 5 CH 2 OH + HCl. Another route entails hydrogenation of benzaldehyde, a by-product of the oxidation of toluene to benzoic acid.
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
Orthoesters can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile. Reduction to benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH 4 or sodium borohydride. Decarboxylation to benzene may be effected by heating in quinoline in the presence of copper salts.
The reaction involving benzaldehyde was discovered by Claisen using sodium benzylate as base. [1] The reaction produces benzyl benzoate. [4] The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is sodium benzylate. Enolizable aldehydes are not amenable to Claisen's conditions.
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. [1] [2] [3] For example, toluene can be oxidized to benzaldehyde. It is named for the French chemist Alexandre Léon Étard (5 January 1852, Alençon – 1 May 1910).
This Ru-encapsulated MOF catalyzes oxidation of benzyl alcohol to benzaldehyde, although degradation of the MOF occurs. The same catalyst was used in the hydrogenation of benzene to cyclohexane . In another example, Pd nanoparticles embedded within defective HKUST-1 framework enable the generation of tunable Lewis basic sites. [ 75 ]