Claisen-Schmidt condensation

In organic chemistry, the Claisen–Schmidt condensation is the reaction between an aldehyde or ketone having an α-hydrogen with an aromatic carbonyl compound lacking an α-hydrogen. This reaction is named after two of its pioneering investigators Rainer Ludwig Claisen and J. G. Schmidt, who independently published on this topic in 1880 and 1881.[1][2][3] An example is the synthesis of dibenzylideneacetone ((1E, 4E)-1,5-diphenylpenta-1,4-dien-3-one).[4]

Quantitative yields in Claisen–Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus benzaldehydes.[5] Because the enolizeable nucleophilic carbonyl compound and the electrophilic carbonyl compound are two different chemicals, the Claisen–Schmidt reaction is an example of a crossed aldol process.

References
  1. Claisen, L.; Claparède, A. (1881). "Condensationen von Ketonen mit Aldehyden" [Condensations of ketones with aldehydes]. Berichte der Deutschen Chemischen Gesellschaft. 14 (1): 2460–2468. doi:10.1002/cber.188101402192.
  2. Schmidt, J. G. (1881). "Ueber die Einwirkung von Aceton auf Furfurol und auf Bittermandelöl in Gegenwart von Alkalilauge" [On the effect of acetone on furfural and on bitter almond oil (benzaldehyde) in the presence of alkali hydroxides]. Berichte der Deutschen Chemischen Gesellschaft. 14 (1): 1459–1461. doi:10.1002/cber.188101401306.
  3. March, J. (1985). Advanced Organic Chemistry: Reactions, Mechanisms and Structure (3rd ed.). Wiley Interscience. ISBN 0-471-85472-7.
  4. Hull, L. A. (February 2001). "The Dibenzalacetone Reaction Revisited". J. Chem. Educ. 78 (2): 226. Bibcode:2001JChEd..78..226H. doi:10.1021/ed078p226.
  5. Rahman A. F. M. Motiur, Ali Roushown, Jahng Yurngdong, Kadi Adnan A. (2012). "A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones". Molecules. 17: 571–583. doi:10.3390/molecules17010571.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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