Methanol → Methyl 3-iodobenzoate

Participants

Reaction Steps

To a solution of 3-iodobenzoic acid (50.0 g, 0.202 mol) in methanol (300.0 ml) was added H2SO4 (1.0 ml). The reaction mixture was heated to reflux. After reflux 24 h, heating was stopped. The reaction mixture was cooled to room temperature. Water (400.0 ml) was added, the product was extracted with ethyl acetate (2×300.0 ml). The organic layer was washed with 20% of NaHCO3 water solution and followed with water. After removal of ethyl acetate, the crude product was purified by recrystallization from ethanol/water. Final white pure product was obtained in 51.0 g (96.5%) after dry under vacuum. 1H NMR (400 MHz, CDCl3, δ): 8.35 (t, J=1.6 Hz, 1H), 7.97 (dt, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.85 (dt, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.14 (t, J=8.4 Hz, 1H), 3.89 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 165.56, 141.70, 138.42, 131.93, 130.03, 128.70, 93.76, 52.38.

Provenance & Evidence