- Source: Stobbe condensation
The Stobbe condensation entails the reaction of an aldehyde or ketone with an ester of succinic acid to generate alkylidene succinic acid or related derivatives. The reaction consumes one equivalent of metal alkoxide. Commonly, diethylsuccinate is a component of the reaction. The usual product is salt of the half-ester. The Stobbe condensation is named after its discoverer, Hans Stobbe, whose work involved the sodium ethoxide-induced condensation of acetone and diethyl succinate.
An example is the reaction of benzophenone with diethyl succinate:
A reaction mechanism that explains the formation of both an ester group and a carboxylic acid group is centered on a lactone intermediate (5):
The Stobbe condensation is also illustrated by the synthesis of the drug tametraline.
See also
Aldol condensation
Polyketide synthase
Dieckmann condensation
Claisen condensation
References
External links
"Claisen Condensation". Organic Chemistry Portal.
Kata Kunci Pencarian:
- Stobbe condensation
- Claisen condensation
- Perkin reaction
- Succinic acid
- Sodium hydride
- Diethyl succinate
- List of organic reactions
- Bisdehydrodoisynolic acid