Nitric Acid → 2-(2-Chloro-5-nitrophenyl)acetic acid

HRID 1257190Notes

Reaction equation

HRID 1257190 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

HCID 944Nitric AcidHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 8271282-(2-Chloro-5-nitrophenyl)acetic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c96fb8cb54f64d079e08dffe146c6248
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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