4-Nitrophenol → 1-(2-Methoxyethoxy)-4-nitrobenzene

Participants

Reaction Steps

A stirred solution of 4-nitrophenol (Fluka) (0.511 g, 3.67 mmol) in DMF (10 mL) was treated with 60% sodium hydride (Aldrich) (0.170 g, 4.25 mmol) added in portions at 0° C. The yellow mixture was stirred at that temperature for 10 min, then 2-bromoethyl methyl ether (Aldrich) (0.380 mL, 4.04 mmol) was added dropwise at 0° C. The mixture was stirred at that temperature for 5 min, warmed up to rt and stirred for 3.5 h then at 70° C. overnight. The reaction mixture was poured into ice-water (100 mL). The aqueous phase was extracted with EtOAc (2×70 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(2-methoxyethoxy)-4-nitrobenzene (0.753 g, 105% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.16-8.25 (m, 2H); 6.95-7.03 (m, 2H); 4.17-4.26 (m, 2H); 3.73-3.84 (m, 2H); 3.46 (s, 3H). m/z (ESI, +ve ion) 198.1 (M+H)+.

Provenance & Evidence