Potassium Hydroxide → (3-Methoxy-4-nitrophenyl)acetic acid

反応式

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

参加物

反応条件

温度: 70 °C

実験手順

A solution of diethyl (3-methoxy-4-nitrophenyl)propanedioate (3.8 g, 12.219 mmol) in 30 mL of methanol and 20 mL of water was added KOH (2.05 g, 36.657 mmol) and the mixture was heated to 70° C. for 4 hours. Cooled to ambient temperature and removed the solvents under reduce pressure. The residue was added 100 mL of water and adjusted to pH=2 with conc. HCl. Extracted with EtOAc and the organic layer was washed with water, brine and dried over anhydrous sodium sulfate, concentrated to give (3-methoxy-4-nitrophenyl)acetic acid. 1H-NMR (400 MHz, MeOD) δ ppm 7.75 (d, J=8.6 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 6.98 (dd, J=7.8 Hz, J=1.6 Hz, 1H), 3.93 (s, 3H), 3.70 (s, 2H).