Tishchenko reaction

History

Examples

• The Tishchenko reaction of acetaldehyde gives the commercially important solvent ethyl acetate. The reaction is catalyzed by aluminium alkoxides.
• The Tishchenko reaction is used to obtain isobutyl isobutyrate, a specialty solvent.
• Hydroxypivalic acid neopentyl glycol ester is produced by a Tishchenko reaction from hydroxypivaldehyde in the presence of a basic catalyst.
• The Tishchenko reaction of paraformaldehyde in the presence of aluminum methylate or magnesium methylate forms methyl formate.
• Paraformaldehyde reacts with boric acid to form methyl formate. 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.

  Related topics

• Aldol–Tishchenko reaction
• Baylis–Hillman reaction
• Cannizzaro reaction
• Meerwein–Ponndorf–Verley reduction
• Oppenauer oxidation