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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 ...
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 .
Usually phenol ethers are synthesized through the condensation of phenol and an organic alcohol; however, other known reactions regarding the synthesis of ethers can be applied to phenol ethers as well. Anisole (C 6 H 5 OCH 3) is the simplest phenol ether, and is a versatile precursor for perfumes and pharmaceuticals. [1]
Sodium phenoxide reacts with alkylating agents to afford alkyl phenyl ethers: [2] NaOC 6 H 5 + RBr → ROC 6 H 5 + NaBr. The conversion is an extension of the Williamson ether synthesis. With acylating agents, one obtains phenyl esters: [citation needed] NaOC 6 H 5 + RC(O)Cl → RCO 2 C 6 H 5 + NaCl
15-Crown-5 is a crown ether with the formula (C 2 H 4 O) 5. It is a cyclic pentamer of ethylene oxide that forms complex with various cations , including sodium (Na + ) [ 2 ] and potassium (K + ); [ 3 ] however, it is complementary to Na + and thus has a higher selectivity for Na + ions.
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]
12-Crown-4 can be synthesized using a modified Williamson ether synthesis, using LiClO 4 as a templating cation: [1] (CH 2 OCH 2 CH 2 Cl) 2 + (CH 2 OH) 2 + 2 NaOH → (CH 2 CH 2 O) 4 + 2 NaCl + 2 H 2 O. It also forms from the cyclic oligomerization of ethylene oxide in the presence of gaseous boron trifluoride. [2]