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The reaction was first described by Emil Fischer and Arthur Speier in 1895. [1] Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary or secondary. Tertiary alcohols are prone to elimination. Contrary to common misconception found in organic chemistry textbooks, phenols can also be esterified to give ...
The reaction is slow in the absence of a catalyst. Sulfuric acid is a typical catalyst for this reaction. Many other acids are also used such as polymeric sulfonic acids. Since esterification is highly reversible, the yield of the ester can be improved using Le Chatelier's principle: Using the alcohol in large excess (i.e., as a solvent).
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
Bases catalyze the reaction by removing a proton from the alcohol, thus making it more nucleophilic. The reaction can also be accomplished with the help of enzymes, particularly lipases (one example is the lipase E.C.3.1.1.3 [2]).
This reaction is exploited in native chemical ligation, a protocol for peptide synthesis. [8] In a related reaction, thioesters can be converted into esters. [9] Thioacetate esters can also be cleaved with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of pent-4-yne-1-thiol: [10]
The Yamaguchi esterification is the chemical reaction of an aliphatic carboxylic acid and 2,4,6-trichlorobenzoyl chloride (TCBC, Yamaguchi reagent) to form a mixed anhydride which, upon reaction with an alcohol in the presence of stoichiometric amount of DMAP, produces the desired ester. It was first reported by Masaru Yamaguchi et al. in 1979 ...
In acidic Shiina esterification, Lewis acid catalysts are used, while nucleophilic catalysts are used for Shiina esterification under basic conditions. Shiina esterification using Lewis acid catalyst. In the acidic reaction, 4-trifluoromethylbenzoic anhydride (TFBA) is mainly used as a dehydration condensation agent.
An esterification reaction is a chemical reaction that creates an ester This category is part of a classification scheme based on the Royal Society of Chemistry RXNO Name Reaction Ontology. Pages in category "Esterification reactions"