Nitric Acid → 2-(2-Chloro-5-nitrophenyl)acetic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A mixture of (2-chlorophenyl)acetic acid (15 g, 88 mmol) in conc. H2SO4 (100 mL) was cooled to −20° C. and treated drop-wise with conc. HNO3 (9.4 g, 97 mmol). The resulting mixture was stirred at −20° C. for 0.5 h, poured into the ice-water, and extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo to give (2-chloro-5-nitrophenyl)acetic acid (15 g, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.58 (s, 1H), 8.35 (m, 1H), 7.96 (m, 1H), 4.12 (s, 2H).