Sodium Hydroxide → 3-Methyl-4-(1,3-oxazol-4-yl)phenol

HRID 497233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497233
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:12])=O.[CH:13]([O-:15])=O.[NH4+:16].[OH-].[Na+]>C(O)=O>[CH3:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:16]=[CH:13][O:15][CH:2]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 178121702-Bromo-1-(4-hydroxy-2-methylphenyl)ethanone

Produkt 1

HCID 223167433-Methyl-4-(1,3-oxazol-4-yl)phenolAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-1-(4-hydroxy-2-methylphenyl)-1-ethanone (18 g, 78 mmol), ammonium formate (17 g, 273 mmol) in formic acid (100 ml) was heated at reflux temperature for 3 hours. The mixture was cooled down to room temperature and made basic by addition of 50% NaOH aqueous solution at 0° c. The whole was extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (1.8 g, 13% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. extractionThe whole was extracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-a6d07bf5ce784fb19e689cb86568db81
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949536B2

Notizen zur Reaktion

Wird geladen…