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

HRID 894928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894928
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 130136843-(2-Cyano-4-trifluoromethylphenoxy)benzoic acidAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Hydroxybenzoic acid (27.6 g), 4-chloro-3-cyano-benzotrifluoride (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 recrystallised to give the benzoic acid derivative (24.0 g) with a melting point of 224°-226° C.

Aufarbeitung

  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 recrystallised

Quellen und Nachweise

ORD-Eintrag
ord-72ccb4973dd04c44a67b9b72b486d370
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04285723

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