Abstract
Ultrasonic and microwave-assisted practical methods have been developed for the O-alkylation of aryl (β-naphthols) and Heteroaryl (hydroxy pyridines) in aqueous surfactant media in good to excellent yields. The developed methods are simple, efficient, economical and environmentally safe. Our novel methods describe a set of green methods to Wil-liamson synthesis.
Highlights
The discovery, development and identification of biologically active compounds gained lot of importance in the recent years
Literature survey shows that Williamson synthesis is probably one of the most common classical methods being used for the preparation of symmetrical and unsymmetrical ethers [3,4,5,6,7,8,9,10,11]
Aqueous surfactants are environmentally benign, non-flammable and possesses remarkable ability to catalyze chemical transformations between some insoluble organic reactants. Encouraged by this aspect we have conducted etherification of βnaphthol and hydroxy pyridine reactions in aqueous micellar media (Scheme 1). For this purpose we have used available in the laboratory bench top chemicals sodium dodecyl sulfate (SDS, anionic), cetyl trimethyl ammonium bromide (CTAB, cationic) and Triton X-100 (Tx-100, non-ionic) surfactants to generate micelles in water
Summary
The discovery, development and identification of biologically active compounds gained lot of importance in the recent years. A good number of homogeneous Bronsted acids or Lewis acid based transition metals have been reported as catalysts in the etherification of alcohols [5,6,7,8,9] These systems exhibited some drawbacks including their deactivation through decomposition by the water formed during the course of reaction. Literature survey shows some reports on the use of phase transfer, polymer and clay supported catalysts for the synthesis of symmetrical and unsymmetrical ethers [1218]. In the present study we were successful to develop an acid free and solvent free synthetic protocols for etherification of phenols and hydroxy pyridines by replacing H2SO4 with a variety of micelle forming surfactants such as sodium dodecyl sulphate (SDS), cetyl trimethyl ammonium bromide (CTAB) and Triton-X 100 (Tx-100) with and without using water as reaction medium. We were successful to conduct ultrasonically assisted (USAR) and microwave assisted reactions (MWAR)
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