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Named reaction in organic chemistry
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 . It can be considered as a specific variation of the
aldol condensation . This reaction is named after two of its pioneering investigators
Rainer Ludwig Claisen and
J. Gustav Schmidt , who independently published on this topic in 1880 and 1881.
[1]
[2]
[3] [
page needed ] 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 enolizable 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
^ 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 .
^ 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 .
^ March, J. (1985). Advanced Organic Chemistry: Reactions, Mechanisms and Structure (3rd ed.). Wiley Interscience.
ISBN
0-471-85472-7 .
^ Hull, L. A. (February 2001).
"The Dibenzalacetone Reaction Revisited" .
J. Chem. Educ. 78 (2): 226.
Bibcode :
2001JChEd..78..226H .
doi :
10.1021/ed078p226 .
^ 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 (1): 571–583.
doi :
10.3390/molecules17010571 .
PMC
6269007 .
PMID
22231494 . {{
cite journal }}
: CS1 maint: multiple names: authors list (
link )