Nitric Acid → 2,5-Dichloro-3-nitrobenzoic acid

HRID 535734

Reaction equation

HRID 535734 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 57842,5-Dichlorobenzoic acid

Product 1

HCID 69512,5-Dichloro-3-nitrobenzoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,5-dichlorobenzoic acid (3 g, 15.7 mmol) in H2SO4 (16 mL) at 0° C. was added dropwise fuming nitric acid (1.4 mL, 31.4 mmol) and the reaction mixture was stirred for 5 minutes at 0° C., and was then gradually allowed to warm to over 20 minutes. The reaction was treated with ice water and extracted with EtOAc. The organic layer was washed with water and brine then dried (Na2SO4), filtered and concentrated to afford 3.54 g (48%) of 2,5-dichloro-3-nitrobenzoic acid which is contaminated with 3,6-dichloro-2-nitrobenzoic acid (40%): 1H NMR (300 MHz, CD3OD) δ 7.73 (s, 1H) 8.06 (d, J=2.6 Hz, 1H) 8.11 (d, J=2.6 Hz, 1H).

Workup

  1. temperatureto warm to over 20 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a77fc82b008641b5992a201a3f0fe36f
Source dataset
uspto-grants-2014_10
Patent number
US08859548B2

Linked notes

Loading…