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The Williamson reaction is of broad scope, is widely used in both laboratory and industrial synthesis, and remains the simplest and most popular method of preparing ethers. Both symmetrical and asymmetrical ethers are easily prepared. The intramolecular reaction of halohydrins in particular, gives epoxides.
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.
The Seyferth–Gilbert homologation is a chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3. [ 1 ] [ 2 ] Dimethyl (diazomethyl)phosphonate 2 is often called the Seyferth–Gilbert reagent .
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.
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 ...
Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH 3 OCH 3, (sometimes ambiguously simplified to C 2 H 6 O as it is an isomer of ethanol). The simplest ether , it is a colorless gas that is a useful precursor to other organic compounds and an aerosol propellant that is currently being demonstrated for ...
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Williamson ether synthesis [ edit ] This ether may also be prepared by way of the Williamson ether synthesis in which n -propoxide, the conjugate base of n -propanol, is reacted with an n -propyl halide: [ 3 ]