Examples
- Benzaldehyde reacts with sodium benzyloxide (generated from sodium and benzyl alcohol) to benzyl benzoate.[2]
- The Tishchenko reaction of acetaldehyde gives the commercially important solvent ethyl acetate; it is catalyzed by aluminium alcoholate.[3]
- The Tishchenko reaction is used to obtain isobutyl isobutyrate, a specialty solvent.[4]
- Hydroxypivalic acid neopentyl glycol ester is produced by a Tishchenko reaction from hydroxypivaldehyde in the presence of a basic catalyst (e.g., aluminium oxide).[5]
- The Tishchenko reaction of paraformaldehyde in the presence of aluminum methylate or magnesium methylate forms methyl formate.[6]
- Paraformaldehyde reacts with boric acid to methyl formate.[7] The key step in the reaction mechanism for this reaction is a 1,3-hydride shift in the hemiacetal intermediate formed from two successive nucleophilic addition reactions, the first one from the catalyst. The hydride shift regenerates the alkoxide catalyst.
