Acetic Acid → Methyl (2-ethyl-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

HRID 2076630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076630
C(O)(=O)C.Br.[CH2:6]([C:8]1[CH:13]=[C:12](CC#N)[CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1)[CH3:7].[C:25]([O:28][CH2:29]C)(=[O:27])[CH3:26]>>[CH2:6]([C:8]1[CH:13]=[C:12]([CH2:26][C:25]([O:28][CH3:29])=[O:27])[CH:11]=[CH:10][C:9]=1[C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[CH3:7]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 67119130(2-Ethyl-4'-methoxy-1,1'-biphenyl-4-yl)acetonitrile

Produkt 1

HCID 86088088Methyl (2-ethyl-4'-hydroxy-1,1'-biphenyl-4-yl)acetateAusbeute 85 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Acetic acid (55 ml) and hydrobromic acid (55 ml) were added to (2-ethyl-4′-methoxy-1,1′-biphenyl-4-yl)acetonitrile (5.5 g, 22 mmol) obtained in Example (26-3), and the mixture was stirred at 100° C. for 10 hours. After the reaction mixture was cooled to room temperature, ethyl acetate was added thereto and the mixture was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. After methanol (150 ml) was added to the residue obtained by removing the solvent under reduced pressure, sulfuric acid (3 ml) was added to the mixture under ice-cooling. After the mixture was stirred at room temperature for 1 hour, the solvent was removed under reduced pressure. After ethyl acetate was added to the obtained residue, the mixture was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1-2/1) to give methyl (2-ethyl-4′-hydroxy-1,1′-biphenyl-4-yl)acetate as a colorless solid (5.0 g, yield: 85%).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. washthe mixture was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. additionAfter methanol (150 ml) was added to the residue
  5. customobtained
  6. customby removing the solvent under reduced pressure, sulfuric acid (3 ml)
  7. additionwas added to the mixture under ice-
  8. temperaturecooling
  9. stirringAfter the mixture was stirred at room temperature for 1 hour
  10. customthe solvent was removed under reduced pressure
  11. additionAfter ethyl acetate was added to the obtained residue
  12. washthe mixture was washed with a saturated aqueous NaCl solution
  13. dry with materialdried with anhydrous sodium sulfate
  14. customThe residue obtained
  15. customby removing the solvent under reduced pressure
  16. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1-2/1)

Quellen und Nachweise

ORD-Eintrag
ord-2fd5a02bc9fb49e8bccc975019bfd490
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923573B2

Notizen zur Reaktion

Wird geladen…