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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 ...
18-Crown-6 can be synthesized by the Williamson ether synthesis using potassium ion as the template cation. Structure of nickel-aquo nitrate complex of the ligand derived from the templated trimerization of 2-aminobenzaldehyde. [5] The phosphorus analogue of an aza crown can be prepared by a template reaction. [6]
Williamson ether synthesis; R−Br + OR' − → R−OR' + Br − (S N 2) The Wenker synthesis, a ring-closing reaction of aminoalcohols. The Finkelstein reaction, a halide exchange reaction. Phosphorus nucleophiles appear in the Perkow reaction and the Michaelis–Arbuzov reaction. The Kolbe nitrile synthesis, the reaction of alkyl halides ...
When the metal atom is not desired in the final product, a disadvantage of templated synthesis is the difficulty in removing the templating metal from the macrocyclic ligand. 18-Crown-6 can be synthesized by the Williamson ether synthesis using potassium ion as the template cation.
However, this synthesis risks the self-condensation of alcohol itself (e.g. ethanol self-condenses to form diethyl ether). 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 ...
When the alkylating agent is an alkyl halide, the conversion is called the Williamson ether synthesis. Alcohols are also good alkylating agents in the presence of suitable acid catalysts. For example, most methyl amines are prepared by alkylation of ammonia with methanol.
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 .