4-Ethoxyphenol → Methyl 3,5-dinitro4-(4-ethoxyphenoxy)benzoate

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A mixture of 13 g (50 mmole) of methyl 4-chloro-3,5-dinitrobenzoate, 7.45 g (54 mmole) of 4-ethoxyphenol, and 13 ml of potassium hydroxide solution (3.03 g, 54 mmole) was heated under argon at 150° C. for 4 h. The mixture was cooled and partitioned between 130 ml of 2 N sodium hydroxide solution and 400 ml of dichloromethane. The organic layer was washed with 2×100 ml of saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated under high vacuum to give 14.5 g, which was chromatographed on a silica gel column (5 cm×50 cm), eluting with 25% hexane/75% dichloromethane to give 13.2 g (74% yield). TLC (silica gel, CH2Cl2), Rf0.80. NMR: 1H (300 MHz) (CDCl3) 1.39 (3H, t, —CH3); 3.97 (2H, q, —CH2—); 4.02 (3H, s, —OCH3); 6.81 (4H, s, arom); and 8.70 ppm (2H, s, arom).

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