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The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol . This reaction was developed by Alexander Williamson in 1850. [ 2 ] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction .
Alexander Williamson. Williamson is credited for his research on the formation of unsymmetrical ethers by the interaction of an alkoxide with a haloalkane, known as the Williamson ether synthesis. He regarded ethers and alcohols as substances analogous to and built up on the same type as water, and he further introduced the water-type as a ...
A more common and higher-yielding reaction is the Williamson ether synthesis, where a phenol is converted by a strong base to the phenoxide ion, which can subsequently be reacted with an alkyl halide via nucleophilic substitution to form the desired phenol ether.
Synthesis from the latter chemical is accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent. [3] [4] [5] Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane. [6]
Alexander Williamson may refer to: Alexander William Williamson (1824–1904), chemist who discovered the Williamson ether synthesis reaction Alexander Williamson (missionary) (1829–1890), Scottish Protestant missionary to China with the London Missionary Society
Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis. [1] [2] Transition metal alkoxides are widely used for coatings and as catalysts. [3] [4]
This reaction, the Williamson ether synthesis, involves treatment of a parent alcohol with a strong base to form the alkoxide, followed by addition of an appropriate aliphatic compound bearing a suitable leaving group (R–X). Although popular in textbooks, the method is usually impractical on scale because it cogenerates significant waste.
This reaction is the reverse of the formation reaction from an epoxide and can be considered a variant of the Williamson ether synthesis. Most of the world's supply of propylene oxide arises via this route. [7] Such reactions can form the basis of more complicated processes, for example epoxide formation is one of the key steps in the Darzens ...