4-Nitrophenol → HCID 117716265, compound

Participants

Reaction Steps

Into a mixture of 4-nitrophenol (60.5 g), potassium carbonate (180 g), potassium iodide (15 g), and disodium phosphate (15 g) in acetone (1000 ml) was added 6-bromohexanoic acid 2-[2-(6-bromohexanoyloxy)-ethoxy]-ethyl ester (100 g). The solution was stirred at reflux for 24 hours. The acetone layer was distilled off and cold water (250 ml) was added. The crude product was extracted into chloroform and the chloroform extract was washed with 5% sodium bicarbonate solution (800 ml) followed by water (600 ml). The chloroform layer was dried over anhydrous sodium sulphate and distilled, and the final product was precipitated by adding diisopropyl ether. The crude product was isolated by filtration and drying. The final product was recrystallized using a mixture of ethyl acetate and diisopropyl ether (1:3) to give pure 6-(4-nitrophenoxy)-hexanoic acid 2-{2-[6-(4-nitrophenoxy)-hexanoyloxy]-ethoxy}-ethyl ester (100 grams) as a white powder. The product was characterized by 1H NMR (CDCl3) δ 1.50 (m, 2H, CH2), 1.70 (m, 2H, CH2), 1.82 (m, 2H, CH2), 2.38 (t, 2H, CH2), 3.74 (t, 2H, CH2), 4.08 (t, 2H, CH2), 4.26 (t, 2H, CH2), 6.92 (d, 2H, Ar), 8.20 (d, 2H, Ar). The product has a melting point of 60-62° C.

Provenance & Evidence