Sodium Hydroxide → 2-(4-Methoxy-2-nitrophenyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl (4-methoxy-2-nitrophenyl)malonate (1.1 g; 3.53 mmol; 1 eq) in a mixture of EtOH (25 mL) and sodium hydroxide (25 mL; 1 M; 25 mmol; 7.07 eq) is heated for 1 h at 90° C. The solvents are removed under reduced pressure and the orange-yellow powder is suspended in THF (20 mL). After cooling down to 0° C., 5M HCl (20 mL) is added. The reaction mixture is refluxed at 85° C. for 1 h. After cooling down to room temperature, the 2 phases are separated and the organic phase is dried over MgSO4. The aqueous phase is treated twice with EtOAc (50 mL) and the combined organic phases are dried over MgSO4 then concentrated to dryness to afford 850 mg (100%) of the title compound as a brown solid. 1H NMR (DMSO-d6) δ 8.20-8.10 (m, 1H), 7.45 (d, J=3.0 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.95 (dd, J=8.0, 3.0 Hz, 1H), 3.78 (s, 2H), 3.67 (s, 3H). HPLC (max plot) 89%; Rt 2.54 min. LC/MS: (ES+): 229.0 (M+NH4+).

Provenance & Evidence