Water → 2-Chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid

HRID 868393Notes

Reaction equation

HRID 868393 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[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].[Cl:22]Cl.O>C(O)(=O)C>[Cl:22][C:11]1[CH:12]=[CH:13][C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([C:18]([F:20])([F:19])[F:21])=[CH:17][C:2]=2[Cl:1])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 24526ChlorineHCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

Product 1

HCID 130136822-Chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3(2-chloro-4-trifluoromethylphenoxy)benzoic acid (5 g) in glacial acetic acid (30 ml) was heated under reflux while chlorine was passed through the solution for 5 hours. The solution was left to stand for two days at room temperature and then poured into cold water (500 ml). An off-white gummy solid separated. This was extracted with ethyl acetate and the extract dried and evaporated. The brown oil remaining was dissolved in sodium bicarbonate solution and the solution extracted with ethyl acetate. The aqueous solution was acidified with hydrochloric acid. The solution was decanted from the precipitated gum, and the gum taken up in boiling hexane. The hexane solution was filtered and allowed to cool. The required 2-chloro-5(2-chloro-4-trifluoromethylphenoxy)benzoic acid was obtained (1.0 g) as crystals of melting point 103°-104°. This acid was used as starting material for compounds 7 and 8.

Workup

  1. waitThe solution was left
  2. waitto stand for two days at room temperature
  3. customAn off-white gummy solid separated
  4. extractionThis was extracted with ethyl acetate
  5. customthe extract dried
  6. customevaporated
  7. dissolutionThe brown oil remaining was dissolved in sodium bicarbonate solution
  8. extractionthe solution extracted with ethyl acetate
  9. customThe solution was decanted from the precipitated gum
  10. filtrationThe hexane solution was filtered
  11. temperatureto cool

Sources & evidence

ORD record
ord-1597c40a18db467da490f3e7eb9dbf92
Source dataset
uspto-grants-1988_10
Patent number
US04778914

Reaction notes

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