4-Nitrophenol → 6-(4-Nitrophenoxy)-hexanoic acid methyl ester

Participants

Reaction Steps

To a mixture of 4-nitrophenol (150 g), Potassium carbonate (600 g), sodium iodide (10 g) in anhydrous acetone (2.1 liter) was added methyl 6-bromohexanoate (156 g) and heated to reflux for 48 hours. Acetone was distilled and water (2 liter) was added. Crude 6-(4-nitrophenoxy)-hexanoic acid methyl ester was filtered, dried and recrystallised from a mixture of ethyl acetate and hexane (1:6) to obtain pure 6-(4-nitrophenoxy)-hexanoic acid methyl ester (130 g) as a white powder with a melting point of 84.5.5-86.6° C. The product was characterized by 1H NMR (CDCl3) δ 1.56 (m, 2H, CH2), 1.74 (m, 2H, CH2), 1.90 (s, 2H, CH2), 3.68 (s, 3H, Ester), 4.06 (t, 2H, CH2), 6.92 (d, 2H, Ar), 8.20 (d, 2H, Ar).

Provenance & Evidence