Sodium Bicarbonate → 2-(3-Acetyl-4-hydroxyphenyl)propan-1-ol

HRID 26675

Reaktionsgleichung

Reaktionsgleichung von HRID 26675
C([O:4][CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15](=[O:17])[CH3:16])[CH:9]=1)[CH3:7])(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[C:15]([C:10]1[CH:9]=[C:8]([CH:6]([CH3:7])[CH2:5][OH:4])[CH:13]=[CH:12][C:11]=1[OH:14])(=[O:17])[CH3:16]

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 213220012-(3-Acetyl-4-hydroxyphenyl)propyl acetate

Produkt 1

HCID 213220152-(3-Acetyl-4-hydroxyphenyl)propan-1-olAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-(3-Acetyl-4-hydroxyphenyl)propyl acetate (20.0 g; 0.0847 mol) and sodium bicarbonate (25.4 g; 0.31 mol) were dissolved in ethanol (200 ml) and water (150 ml), and the mixture was refluxed for 20 hours. Ethanol was removed in vacuo and the residue was extracted with ether (3×150 ml). The combined ether extracts were washed with water, saturated sodium bicarbonate solution, brine, and then dried over magnesium sulphate. The product, after removing solvent, was chromatographed on silica gel using ether as eluent to give a pale brown oil (15.0 g; 72% yield).

Aufarbeitung

  1. customEthanol was removed in vacuo
  2. extractionthe residue was extracted with ether (3×150 ml)
  3. washThe combined ether extracts were washed with water, saturated sodium bicarbonate solution, brine
  4. dry with materialdried over magnesium sulphate
  5. customThe product, after removing solvent
  6. customwas chromatographed on silica gel
  7. customto give a pale brown oil (15.0 g; 72% yield)

Quellen und Nachweise

ORD-Eintrag
ord-c8cdc35903ee4384a5334e8fcf4bd332
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151179

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