Hydrochloric Acid → 6-(4-Methoxy-2-nitrophenoxy)-2-phenylchroman

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Reaction Conditions

Reaction Steps

The 2-phenylchroman-6-ol (500 mg) and 1-chloro-4-methoxy-2-nitrobenzene (390 mg) were dissolved in DMSO (10 ml). Potassium hydroxide (230 mg) and potassium iodide (520 mg) were added and the resulting mixture was stirred at 90° C. for 1 hour. After cooling it was poured in to 1 M HCl-solution (20 ml) and extracted with dichloromethane. The combined organic layers were washed with water until neutral and then with saturated NaCl-solution and dried with Na2SO4. After evaporating the solvents the 6-(4-Methoxy-2-nitrophenoxy)-2-phenylchroman was obtained by trituration with methanol. 1H NMR (400 MHz, d6-DMSO) δ: 7.58 (d, 1H, J 3.1 Hz), 7.45-7.33 (m, 6H), 7.28 (dd, 1H, J 9.2 Hz, 3.1 Hz), 7.10 (d, 1H, J 9.2 Hz), 6.86-6.78 (m, 3H), 5.10 (dd, 1H, J 10.0, 1.9 Hz), 3.83 (s, 3H), 2.92 (ddd, 1H, J −16.9, 11.2, 5.9 Hz), 2.75 (ddd, 1H, J −16.9, 7.9, 4.2 Hz), 2.15 (m, 1H), 1.97 (m, 1H).

Provenance & Evidence