4-Nitrophenol → Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate

Participants

Reaction Steps

To a mixture of 4-Nitrophenol (5 grams, 36 mmol), anhydrous K2CO3 (20 grams, 145 mmol) and sodium iodide (2 grams, 13.3 mmol) in anhydrous acetone (100 mL) was added (2-Bromoethoxy)acetic acid methyl ester (11 grams, 56 mmol) and refluxed for 24 hours. Acetone was distilled and water (100 mL) was added. Crude 74 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant give pure 74 (4 grams, 43.6%) as a white fluffy powder. The melting point was found to be 96-97.8° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3+DMSO) δ 3.72 (s, 3H, ester), 3.94 (t, 2H, OCH2), 4.18 (s, 2H, OCH2), 4.30 (t, 2H, OCH2), 7.08 (d, 2H, Ar), 8.18 (d, 2H, Ar).

Provenance & Evidence