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Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. [1] Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile.
Unlike acid-catalyzed ester hydrolysis, it is not an equilibrium reaction and proceeds to completion. Hydroxide ion attacks the carbonyl carbon to give a tetrahedral intermediate, which then expels an alkoxide ion. The resulting carboxylic acid quickly protonates the alkoxide ion to give a carboxylate ion and an alcohol. [1]
The synthesis of methyl benzoate by Fischer–Speier esterification. Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer and Arthur Speier in 1895. [1]
In organic chemistry, carbonyl reduction is the conversion of any carbonyl group, usually to an alcohol. It is a common transformation that is practiced in many ways. [1] Ketones, aldehydes, carboxylic acids, esters, amides, and acid halides - some of the most pervasive functional groups, -comprise carbonyl compounds.
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 ...
One way is the synthesis from cinnamyl alcohol 1 and vinyl acetate. This reaction is catalyzed by the enzyme triacylglycerol ester hydrolase, which is a lipase that is very specific towards the ester bond. The byproduct of this reaction is acetaldehyde. The reaction equation for this reaction is: [18]
Ortho esters can be prepared by the Pinner reaction, in which nitriles react with alcohols in the presence of one equivalent of hydrogen chloride. The reaction proceeds by formation of imido ester hydrochloride: RCN + R ′ OH + HCl → [RC(OR ′)=NH 2] + Cl −. Upon standing in the presence of excess alcohol, this intermediate converts to ...
The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. [1] It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. [2] [3] [4] Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. [5]