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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.
The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base within the water phase neutralizes the acid, generated in the reaction, while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether.
The primary advantages of Fischer esterification compared to other esterification processes are based on its relative simplicity. Straightforward acidic conditions can be used if acid-sensitive functional groups are not an issue; sulfuric acid can be used; weaker acids can be used with a tradeoff of longer reaction times.
The reaction stoichiometry implicates the Cr(IV) species "CrO 2 OH −", which comproportionates with the chromic acid to give a Cr(V) oxide, which also functions as an oxidant for the alcohol. [ 6 ] The oxidation of the aldehydes is proposed to proceed via the formation of hemiacetal -like intermediates, which arise from the addition of the O ...
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]
This reaction is related to several classic named reactions: The acylated reaction product can be converted into the alkylated product via a Clemmensen or a Wolff-Kishner reduction. [17] The Gattermann–Koch reaction can be used to synthesize benzaldehyde from benzene. [18] The Gatterman reaction describes arene reactions with hydrocyanic acid ...
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 ...
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 ...