Progress toward the Total Synthesis of 5′-Hydroxyzearalenone

作者:

K TadpetchP SudkaowV Rukachaisirikul

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摘要:

Several methods have been developed to convert alcohols into carbonyl compounds. Those methods use different types of oxidizing agents, catalysts and/or solvent systems. Most of them encounter some drawbacks such as using toxic reagents, requiring drastic conditions, non-recycle of reagents or catalysts, using solvents which have volatility, toxicity and non-recoverability problems. Using 1-hexyl-3-methylimidazolium bromide: [hmim][Br], combining with FeCl3 acting as a new catalytic reagent system was considered to solve those problems. 1-Phenylethanol being carried out with 1.5 mol% FeCl3, 3 equivalents of tert-butyl hydroperoxide (TBHP) in [hmim][Br] within 2 h at 80 oC gave 100% conversion into the desired carbonyl compound. The catalytic system could be recycled and reused at least nine times without significant losing of the product yield. The optimized condition was further investigated with other types of alcohols. For primary alcohols, carboxylic acids were detected as main products around 40% to quantitative yield. For secondary alcohols other than 1-phenylethanol, the corresponding ketones were achieved (60% - quantitative yield) while tertiary alcohols are intact within the conditions examined.

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