Synthetic studies in substituted phenols, involving electrophilic side-chain and ring substitutions

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Title: Synthetic studies in substituted phenols, involving electrophilic side-chain and ring substitutions
Author: Warote, Bussakorn
Abstract: This work deals with two separate aspects of the chemistry of phenolic compounds. In the first section a study is reported of aryl alkyl ether synthesis using as a standard nucleophile catechol anion and as electrophilic species a range of alkyl halides. The reactions involved constituted good routes to a number of catechol mono- and di-alkyl catechol ethers. The reaction were studied systematically and key reactivity factors such as steric effects and the influence of changing alkyl chain lengths were evaluated. The high-boiling colorless products were characterize by elemental analysis, H NMR and IR spectra. As a guide to understanding the reactivity of the alkyl halides employed, kinetic runs were performed under essentially the synthetic condition, that is, with the alkyl bromides as substrates in 95% aqueous ethanol con taining a slight excess of sodium hydroxide. Under these conditions, n-propyl bromide proved the most reactive, being about 30% more so than the C., Cg( Cg and Cg unbranched bromides (all of which reacted equally rapidly). The three branched chain halides namely, isopropyl, isobutyl and isopentyl bromides were all substantially less active than the unbranched (clearly for steric reasons). The second section deals with phenolic electrophilic attack also but this time the electrophile attacks the phenolic ring rather than the oxyanion side chain. The work reported deals with the synthesis of a new UV-blocking monomer for use in polymer networks. The essential reaction involved amidomethylation (i.e. attack by an RCONHCH^ species, using N-hydro.xyinethylacrylamide in concentrated sulfuric acid as the electrophile) of a p-cresol ring to which is also attached at an ortho-position a benzotriazole ring. The reaction worked well. The product was cleaved with concentrated hydrochloric acid to yield the parent amine. Auxiliary runs were made (using the same electro phile) with p-cresol without any triazole substituent.
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Date: 1983-12

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