3-Hydroxybenzoic Acid → 3(2-Chloro-5-trifluoromethylphenoxy)benzoic acid

HRID 358196Notes

Reaction equation

HRID 358196 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1F>CO.CS(C)=O.O>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][C:25]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

8

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 27365454-Chloro-3-fluorobenzotrifluoride

Product 1

HCID 193892503(2-Chloro-5-trifluoromethylphenoxy)benzoic acidYield 56.9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Hydroxybenzoic acid (3.45 g) was added to a solution of potassium hydroxide (2.8 g) in methanol. The solution was evaporated under reduced pressure to give a white solid. This was taken up in dry dimethylsulphoxide (25 ml). The resulting solution was stirred and heated at 170° with anhydrous potassium carbonate (1.25 g) and 4-chloro-3-fluorobenzotrifluoride (5 g) for 12 hours. The mixture was then cooled and poured into water, (500 ml). The mixture was extracted with ether and then acidified (HCl). The precipitate which formed was recrystallised from petroleum (b.p. 60°-80°) to give the required acid (4.5 g) with a melting point of 142°-143°.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customto give a white solid
  3. temperatureThe mixture was then cooled
  4. extractionThe mixture was extracted with ether
  5. customThe precipitate which formed
  6. customwas recrystallised from petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-4c414571f23a41c0bc1fbec9940b552e
Source dataset
uspto-grants-1984_08
Patent number
US04465508

Reaction notes

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