The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the. An aldol condensation is a condensation reaction in organic chemistry in which an enol or an Quantitative yields in Claisen–Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus . The Claisen Condensation. Claisen condensation of esters. Reaction type: Nucleophilic Acyl Substitution. Summary. The Claisen condensation is the ester.

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Depending on the nature of the desired product, the aldol condensation may claiden-schmidt carried out under two broad types of conditions: Condensacionn and ethyl esters, which yields methoxide and ethoxide, respectively, are commonly used. Dehydration may be accompanied by decarboxylation when an activated carboxyl group is present. In the process, in addition to water, an equivalent of ethanol and carbon dioxide are lost in decarboxylation. Berichte der Deutschen Chemischen Condensaion. Journal of Organic Chemistry.

Schmidtwho independently published on this topic in and Ethyl glyoxylate 2 and diethyl 2-methylglutaconate 1 react to isoprenetricarboxylic acid 3 isoprene skeleton with sodium ethoxide. Advanced Organic Chemistry Part A: In industry the Aldox process developed by Royal Dutch Shell and Exxonconverts propylene and syngas directly to 2-ethylhexanol via hydroformylation to butyraldehydealdol condensation to 2-ethylhexenal and finally hydrogenation.


Reactions, Mechanisms and Structure 3rd ed. The first step is formation of the Transition metal carbene complex 2. This is believed to be due to steric strain resulting from the methyl group and the carboxylic caisen-schmidt in the cis -dienoid structure. This reaction is named after two of its pioneering investigators Rainer Ludwig Claisen and J.

Not to be confused with Claisen rearrangement.

Claisen condensation – Wikipedia

Quantitative yields in Claisen—Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus benzaldehydes. You can help by adding to it. Upper Saddle River, NJ: Because it is only the cis isomer that precipitates from solution, this product is formed exclusively.

By using this site, you agree to the Terms of Use and Privacy Policy. The aldol addition product can be dehydrated via two mechanisms; a strong base like potassium t -butoxidepotassium hydroxide or sodium hydride in an enolate mechanism, [13] claisen-schnidt or in an acid-catalyzed claaisen-schmidt mechanism.

In other projects Wikimedia Commons. This page was last edited on 29 Aprilat This obstacle is overcome by using a strong base such as potassium hydroxide and a very polar solvent such as DMSO in condenxacion reaction below: For this reason, the conjugate sodium alkoxide base of the alcohol formed e. By using this site, you agree to the Terms of Use and Privacy Policy.

Berichte der Deutschen Chemischen Gesellschaft.

From Wikipedia, the free encyclopedia. In mixed Claisen condensations, a non-nucleophilic base such as lithium diisopropylamideor LDA, may be used, since only one compound is enolizable. Due to epimerization through a common enolate ion intermediate A the reaction product has RR – cis -configuration and not RS – trans -configuration as in the starting material.


The name aldol condensation is also commonly used, especially in biochemistryto refer to just the first addition stage of the process—the aldol reaction itself—as catalyzed by aldolases. Organic Chemistry 6th ed. Then 2N hydrochloric acid is added and the mixture extracted with diethyl ether. This reaction product is very unstable with initial loss of carbon dioxide and followed by many secondary reactions.

Then campholenic aldehyde 1 is added and the mixture refluxed for 15 h.

File:Claisen condensation mechanism.png

claisrn-schmidt Aldol condensations are important in organic synthesisbecause they provide a good way to form carbon—carbon bonds. In this reaction an alkynal 1 is converted into a cycloalkene 7 with a ruthenium catalyst and the actual condensation takes place with intermediate 3 through 5.

This page was last edited on 31 Decemberat Next, the carbonyl carbon of the other ester is nucleophilically attacked by the enolate anion. Justus Liebigs Annalen der Chemie. Support for the reaction mechanism is based on isotope labeling.