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

HRID 370090

Reaction equation

HRID 370090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 58113,5-Dichlorobenzoic acid

Product 1

HCID 52108523,5-Dichloro-2-nitrobenzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3,5-dichlorobenzoic acid (50 g, 0.26 mol) in sulfuric acid (250 mL) at 0° C. was added nitric acid (18 g, 0.28 mol) dropwise, and the mixture warmed slowly to ambient temperature. After 5 hours the mixture was poured onto ice, and the white precipitate collected by filtration. The solid was washed with water (3×30 mL), and dried in vacuo to afford 55 g (90% yield) of 3,5-dichloro-2-nitrobenzoic acid; NMR (CDCl3) 8.3 (s, 1), 8.0 (s, 1) ppm.

Workup

  1. additionAfter 5 hours the mixture was poured onto ice
  2. filtrationthe white precipitate collected by filtration
  3. washThe solid was washed with water (3×30 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-870f3e13df194581981554d219872489
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Linked notes

Loading…