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. Vyacheslav Tishchenko discovered that aluminium
alkoxides allowed the conversion of enolizable aldehydes to esters.
Examples
The Tishchenko reaction of
acetaldehyde gives the commercially important solvent
ethyl acetate. The reaction is catalyzed by aluminium alkoxides.[5]
The Tishchenko reaction is used to obtain isobutyl isobutyrate, a specialty solvent.[6]
Hydroxypivalic acid neopentyl glycol ester is produced by a Tishchenko reaction from hydroxypivaldehyde in the presence of a basic catalyst (e.g.,
aluminium oxide).[7]
В. Е. Тищенко and Г. Н. Григорьева (V. E. Tishchenko and G. N. Grigor'eva) (1906)
"О действии амальгамы магния на изомасляного альдегида" (On the effect of magnesium amalgam on isobutyric aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 540–547. (in Russian)
М. П. Воронҝова and В. Е. Тищенко (M. P. Voronkova and V. E. Tishchenko) (1906)
"О действии амальгамы магния на уксусный альдегид" (On the effect of magnesium amalgam on acetic aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 547–550. (in Russian)
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. Vyacheslav Tishchenko discovered that aluminium
alkoxides allowed the conversion of enolizable aldehydes to esters.
Examples
The Tishchenko reaction of
acetaldehyde gives the commercially important solvent
ethyl acetate. The reaction is catalyzed by aluminium alkoxides.[5]
The Tishchenko reaction is used to obtain isobutyl isobutyrate, a specialty solvent.[6]
Hydroxypivalic acid neopentyl glycol ester is produced by a Tishchenko reaction from hydroxypivaldehyde in the presence of a basic catalyst (e.g.,
aluminium oxide).[7]
В. Е. Тищенко and Г. Н. Григорьева (V. E. Tishchenko and G. N. Grigor'eva) (1906)
"О действии амальгамы магния на изомасляного альдегида" (On the effect of magnesium amalgam on isobutyric aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 540–547. (in Russian)
М. П. Воронҝова and В. Е. Тищенко (M. P. Voronkova and V. E. Tishchenko) (1906)
"О действии амальгамы магния на уксусный альдегид" (On the effect of magnesium amalgam on acetic aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 547–550. (in Russian)