2-Acetylhydroquinone → 2-(4-Trifluoromethylphenyl)-6-hydroxychroman-4-one

Beteiligte Stoffe

Reaktionsschritte

6-Hydroxy-2-(4-trifluoromethylphenyl)chroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 2.0 g of 2′,5′-dihydroxyacetophenone and 2.1 ml of 4-trifluoromethylbenzaldehyde. The product was purified by column chromatography using heptane-ethyl acetate (2:1) as an eluant. Further purification was carried out by column chromatography using toluene-ethyl acetate (4:1) as an eluant. Finally the product was crystallised from ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.47 (s, 1H), 7.82-7.76 (m, 4H), 7.13 (d, 1H, J 3.0 Hz), 7.06 (dd, 1H, J 8.8, 3.0 Hz), 6.99 (d, 1H, J 8.8 Hz), 5.70 (dd, 1H, J 12.9, 2.9 Hz), 3.16 (dd, 1H, J −16.9, 12.9 Hz), 2.86 (dd, 1H, J −16.9, 2.9 Hz).

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