Claisen condensation

Not to be confused with Claisen rearrangement or Claisen–Schmidt condensation.
Claisen condensation
Named after Rainer Ludwig Claisen
Reaction type Condensation reaction
Reaction
R-COO-R′
+
R-COO-R′ or Carbonyl
+
(Base: Na-OR')
↓
β-keto ester
+
R'-OH
Conditions
Typical solvents
R'-OH
Identifiers
Organic Chemistry Portal claisen-condensation
RSC ontology ID RXNO:0000043

The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β-diketone.[1] It is named after Rainer Ludwig Claisen, who first published his work on the reaction in 1887.[2][3][4] The reaction has often been displaced by diketene-based chemistry, which affords acetoacetic esters.[5]

The overall reaction of the classic Claisen condensation

  1. ^ Carey, F. A. (2006). Organic Chemistry (6th ed.). New York, NY: McGraw-Hill. ISBN 0-07-111562-5.
  2. ^ Claisen, L.; Claparede, A. (1881). "Condensationen von Ketonen mit Aldehyden". Berichte der Deutschen Chemischen Gesellschaft. 14 (2): 2460–2468. doi:10.1002/cber.188101402192.
  3. ^ Claisen, L. (1887). "Ueber die Einführung von Säureradicalen in Ketone". Berichte der Deutschen Chemischen Gesellschaft. 20 (1): 655–657. doi:10.1002/cber.188702001150.
  4. ^ Hauser, C. R.; Hudson, B. E. Jr. (1942). "The Acetoacetic Ester Condensation and Certain Related Reactions". Organic Reactions. 1: 266–302. doi:10.1002/0471264180.or001.09. ISBN 0471264180.
  5. ^ Riemenschneider, Wilhelm; Bolt, Hermann M. (2005). "Esters, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_565.pub2. ISBN 3527306730.