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

HRID 1517241Notes

Reaction equation

HRID 1517241 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]>S(=O)(=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 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-(2-chlorophenyl)acetic acid (500 mmol) in conc. sulfuric acid (0.7 mL/mmol) was cooled to −10° C. A freshly prepared mixture of fuming nitric acid fuming (809 mmol) and conc. sulfuric acid (1.6 mol) was slowly added at −10° C. The mixture was allowed to warm to 0° C. over 1 h and was stirred for 4 h at 0° C. The solution was slowly poured onto crushed ice/water (3 L). The mixture was stirred vigorously and the formed precipitate was isolated by filtration. The white solid residue was washed with an excess of water (4 L) and dried, giving 2-(2-chloro-5-nitrophenyl)acetic acid (80%).

Workup

  1. additionwas slowly added at −10° C
  2. additionThe solution was slowly poured
  3. stirringThe mixture was stirred vigorously
  4. customthe formed precipitate was isolated by filtration
  5. washThe white solid residue was washed with an excess of water (4 L)
  6. customdried

Sources & evidence

ORD record
ord-0a3464bbf7df4fa99ad029ed5f0f56e4
Source dataset
uspto-grants-2012_07
Patent number
US08232283B2

Reaction notes

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