2,6-Dihydroxyanthraquinone → 2,6-Bis((2-ethylhexyl)oxy)anthracene-9,10-dione

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2,6-Dihydroxyanthraquinone (100.0 g, 0.42 mol) and 2-ethylhexyl bromide (165.0 g, 0.86 mol) were dissolved in 1 L of DMF. To this solution was added anhydrous K2CO3 (120.0 g, 0.87 mol). The reaction was heated at 90° C. overnight. Most of DMF was removed and 500 mL of water was added. The reaction was extracted with ether (3×400 mL), washed with brine (1×200 mL), and dried over MgSO4. Solvent was removed and the crude product was recrystallized from methanol to give yellow powdery product 125.21 g (65% yield). 1H NMR (CDCl3) δ (ppm): 0.92-0.98 (m, 12H, CH3), 1.34-1.54 (m, 16H), 1.75-1.81 (m, 2H, CH(CH3)), 4.02 (d, J=5.5 Hz, 4H, OCH2), 7.19 (d, J=8.4 Hz, 2H), 7.70 (s, 2H), 8.19 (d, J=8.5 Hz, 2H); 13C NMR (CDCl3): 11.12, 14.06, 23.04, 23.88, 29.08, 30.51, 39.34, 71.34, 110.64, 120.84, 127.00, 129.62, 135.88, 164.29, 182.27. M.p. 49-51° C.; FD-MS: m/z 464 (M+).

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