Methanol → methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate

Beteiligte Stoffe

Reaktionsschritte

To a mixture of (2E)-3-(4-methoxy-2-nitrophenyl)acrylic acid (16 g, 0.067 mol) in dry MeOH (150 mL) under nitrogen is added dropwise thionyl chloride (12.3 mL, 0.169 mol) at 0° C. The reaction mixture is refluxed for 3 h then cooled to room temperature. The solvent is removed under reduced pressure and the residue is taken up in EtOAc. The organic layer is washed with 10% aqueous NaHCO3, water and brine then dried over Na2SO4. The solvent is removed under reduced pressure to afford 14 g (88%) of the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.03-8.07 (m, 1H), 7.58-7.60 (m, 1H) 7.51 (s, 1H), 7.16-7.18 (m, 1H), 6.29-6.33 (m, 1H), 3.91 (s, 3H), 3.82 (s, 3H).

Herkunft & Nachweise