Sodium Hydroxide → 1-Phenyl-1H-pyrazole-3-carboxylic acid

HRID 1178119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178119
[O-:1][Mn](=O)(=O)=O.[K+].[CH3:7][C:8]1[CH:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1.[OH-:19].[Na+]>O>[C:13]1([N:10]2[CH:11]=[CH:12][C:8]([C:7]([OH:1])=[O:19])=[N:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 707833-methyl-1-phenyl-1H-pyrazoleHCID 516875Potassium Permanganate

Produkt 1

HCID 123708741-Phenyl-1H-pyrazole-3-carboxylic acidAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

KMnO4 (1.2 g, 7.6 mmol) was added portionwise to a stirred solution of 3-Methyl-1-phenyl-1H-pyrazole (100 mg, 0.63 mmol) and NaOH (504 mg, 12.6 mmol) in H2O (4 mL). The resulting mixture was heated to 85° C. for 48 hrs. The reaction mixture was filtered, filtrate was acidified with 30% aqueous HCl solution, extracted the aqueous layer with EtOAc. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by washing with hexane to afford 53 mg (44.53% yield) of 1-phenyl-1H-pyrazole-3-carboxylic acid. 1H NMR (DMSO-d6): δ 8.6 (d, 1H), 7.9 (d, 2H), 7.6-7.5 (t, 2H), 7.4 (t, 1H), 6.96 (d, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted the aqueous layer with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified
  7. washby washing with hexane

Quellen und Nachweise

ORD-Eintrag
ord-ba1ce0e2994b4c648b7210d449061c20
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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