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The classic example of a dehydration reaction is the Fischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester RCO 2 H + R′OH ⇌ RCO 2 R′ + H 2 O. Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water.
Water is often used as a solvent, but the presence of water is not necessary; alcohols may also be used as solvents, with dissolved hydroxide ion performing hydrolysis. [ 2 ] In this example of alkaline hydrolysis of ethyl propionate , the asterisk indicates an oxygen-18 atom in an isotope labeling experiment to investigate the mechanism: [ 3 ]
Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann. [1] [2] The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent.
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). [ 1 ] [ 2 ] [ 3 ] The method involves the reaction of an α- amino - ketone (1) and a compound containing an electron-withdrawing group (e.g. an ester as shown) α to a carbonyl group (2) .
Acyloin condensation is a reductive coupling of two carboxylic esters using impure metallic sodium to yield an α-hydroxyketone, also known as an acyloin. [1] [2] [3] The acyloin condensation. The reaction is most successful when R is aliphatic and saturated, and typically performed with a silyl chloride reactant to trap the product as a ...
In addition to the ordinary thermal phenyl ester reaction a photochemical variant is possible. The photo-Fries rearrangement can likewise give [1,3] and [1,5] products, [7] [8] which involves a radical reaction mechanism. This reaction is also possible with deactivating substituents on the aromatic group. Because the yields are low this ...
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H 2 O 2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H 2 O 2 is reduced.
This would be a reversal of the standard esterification mechanism. An example of this method is the acylation of 3-phenylpropanol using glacial acetic acid and TBATB. The reaction generates the ester in 15 minutes in a 95% yield without the need to remove water.