Sulfuric Acid → 5-(2-Chloro-5-trifluoromethylphenoxy)-2-nitrobenzoic acid

HRID 868465Notes

Reaction equation

HRID 868465 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[N+:27]([O-])([O-:29])=[O:28].[K+]>ClCCCl>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:11]([N+:27]([O-:29])=[O:28])=[C:7]([CH:6]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 193892503(2-Chloro-5-trifluoromethylphenoxy)benzoic acid

Product 1

HCID 133898475-(2-Chloro-5-trifluoromethylphenoxy)-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The acid from (b) (2.0 g) was added to a mixture of concentrated sulphuric acid (15 ml) and 1,2-dichloroethane (10 ml) kept at 0°. Potassium nitrate (1.2 g) was then added in portions with stirring over a period of 30 minutes, keeping the temperature at 0°. The mixture was stirred for a further hour at 0° and then for 3 hours at room temperature. The mixture was then poured on to ice and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to give a dark gum. This was extracted several times with boiling cyclohexane. The residue crystallised on cooling and was identified as the required nitro-acid, with a melting point of 147°-148°.

Workup

  1. customkept at 0°
  2. customat 0°
  3. stirringThe mixture was stirred for a further hour at 0°
  4. waitfor 3 hours at room temperature
  5. additionThe mixture was then poured on to ice
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. customdried
  9. customevaporated
  10. customto give a dark gum
  11. extractionThis was extracted several times with boiling cyclohexane
  12. customThe residue crystallised
  13. temperatureon cooling

Sources & evidence

ORD record
ord-29d9992ef21a4f6ea7b8c5b4cbc9f59d
Source dataset
uspto-grants-1988_10
Patent number
US04780128

Reaction notes

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