3-Hydroxybenzoic Acid → 3-(2-Cyano-4-trifluoromethylphenoxy)benzoic acid

HRID 868394Notes

Reaction equation

HRID 868394 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:22]([C:13]1[CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=[CH:17][C:12]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])#[N:23]

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 676042-Chloro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 130136843-(2-Cyano-4-trifluoromethylphenoxy)benzoic acidYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzoic acid (27.6 g), 4-chloro-3-cyanobenzotrifluoride (41.1 g) and anhydrous potassium carbonate (55.2 g) were stirred together for 71/2 hours at 100° C. in dry dimethylformamide (500 ml) and then left at room temperature for 65 hours. The solvent was then removed under reduced pressure and the residue taken up in water and acidified with dilute hydrochloric acid. The solid which separated was washed with water, dissolved in ether and the solution dried and concentrated. The colourless solid which separated was recrystallized to give the benzoic acid derivative (24.0 g) with a melting point of 224°-226° C.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customThe solid which separated
  3. washwas washed with water
  4. dissolutiondissolved in ether
  5. customthe solution dried
  6. concentrationconcentrated
  7. customThe colourless solid which separated
  8. customwas recrystallized

Sources & evidence

ORD record
ord-6f56e0cba8204235b66377b78cf71ebd
Source dataset
uspto-grants-1988_10
Patent number
US04778914

Reaction notes

Loading…