ORGN 117 |
| Daniel S. Tyson, Materials Division, Ohio Aerospace Institute and NASA Glenn Research Center, 21000 Brookpark Road, MS 49-1, Cleveland, OH 44135 and Michael A. Meador, Materials Division, NASA Glenn Research Center, 21000 Brookpark Road, MS 49-3, Cleveland, OH 44135. |
| 4,8-Ditoluoyl-1,5-dihydroxynaphthalene was synthesized in quantitative yield from the corresponding methylenequinone via base-catalyzed hydration. The synthetic approach followed the well established method of methoxy protection of 1,5-dihydroxynaphthalene, acylation, then acid-catalyzed deprotection. The final transformation immediately forms the ring-closed methylenequinone, 6-toluoyl-2-(4-methyl)phenyloxynaphtho[bc]furan-5-one, allowing limited quantities of the substituted dihydroxynaphthalene to be collected (3% yield). Treatment of the methylenequinone with aqueous, alkaline solution gives the title compound in one step with a 99% yield, an improvement of 80% compared to the two step literature method for preparing 4,8-dibenzoyl-1,5-dihydroxynaphthalene. A thorough discussion of related compounds and the complete synthetic methodology will be presented. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |