Tishchenko reaction

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The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide.[1] The reaction product is an ester. Catalysts are aluminium alkoxides or sodium alkoxides.

In the related Cannizzaro reaction the base is sodium hydroxide and then the oxidation product is a carboxylic acid and the reduction product is an alcohol.

Examples[edit]

The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is generated in situ from sodium and benzyl alcohol
The Tishchenko reaction: reaction mechanism

Related reactions[edit]

References[edit]

  1. ^ V. Tishchenko (1908), J. Russ. Phys. Chem. Soc 38: 355, 482 
  2. ^ Kamm, O.; Kamm, W. F. (1941), "Benzyl benzoate", Org. Synth. ; Coll. Vol. 1: 104 
  3. ^ Marc Eckert, Gerald Fleischmann, Reinhard Jira, Hermann M. Bolt, Klaus Golka (2007), "Acetaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 4 
  4. ^ Boy Cornils, Richard W. Fischer, Christian Kohlpaintner (2007), "Butanals", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 4 
  5. ^ Peter Werle, Marcus Morawietz (2007), "Alcohols, Polyhydric", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6 
  6. ^ Günther Reuss, Walter Disteldorf, Armin Otto Gamer, Albrecht Hilt (2007), "Formaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5 
  7. ^ Paul R. Stapp (1973). "Boric acid catalyzed Tishchenko reactions". J. Org. Chem. 38 (7): 1433–1434. doi:10.1021/jo00947a049.