Iodoethane → 2-Ethoxy-1-methoxy-4-nitro-benzene

Participants

Reaction Steps

A mixture of 2-methoxy-5-nitrophenol (5.3 g, 31.3 mmol), iodoethane (14.6 g, 93.9 mmol), and potassium carbonate (43.2 g, 310 mmol) in acetone (100 mL) was heated to reflux for 4 hours. The reaction mixture was cooled, and the solvent was evaporated in vacuo. The residue was dissolved in water (250 mL) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with water (3×75 mL) and dried (MgSO4), and the solvent was evaporated under vacuum, providing 5.8 g of the product, in 99% yield: 1H NMR (CDCl3) δ 1.51 (t, J=7.0 Hz, 3H), 3.97 (s, 3H), 4.18 (q, J=7.0 Hz, 2H), 6.22 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 6.31 (d, J=2.4 Hz, 1H), 6.70 (d, J=8.4 Hz, 1H).

Provenance & Evidence