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. It is named after the Russian organic chemist Vyacheslav Evgen'evich Tishchenko (Вячеслав Евгеньевич Тищенко).[2]

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

Related reactions[edit]

References[edit]

  1. ^ See:
  2. ^ В. Тищенко (V. Tishchenko) (1899) "Действие амальгамированного алюминия на алкоголь. Алкоголятов алюминия, их свойства и реакции." (Effect of amalgamated aluminium on alcohol. Aluminium alkoxides, their properties and reactions.), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 31 : 694–770. (in Russian)
  3. ^ Kamm, O.; Kamm, W. F. (1941). "Benzyl benzoate". Org. Synth.  ; Coll. Vol., 1, p. 104 
  4. ^ Marc Eckert; Gerald Fleischmann; Reinhard Jira; Hermann M. Bolt; Klaus Golka (2007), "Acetaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 4 
  5. ^ Boy Cornils; Richard W. Fischer; Christian Kohlpaintner (2007), "Butanals", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 4 
  6. ^ Peter Werle; Marcus Morawietz (2007), "Alcohols, Polyhydric", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6 
  7. ^ Günther Reuss; Walter Disteldorf; Armin Otto Gamer; Albrecht Hilt (2007), "Formaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5 
  8. ^ Paul R. Stapp (1973). "Boric acid catalyzed Tishchenko reactions". J. Org. Chem. 38 (7): 1433–1434. doi:10.1021/jo00947a049.