Reaktion #62237

Reaktionsgleichung

sodium hydroxide

55

4-Oxo-4-(2,3,4-trimethoxy-phenyl)-butyric acid methyl ester

water

→

56

Ausbeute 94.0%

4-Oxo-4-(2,3,4-trimethoxy-phenyl)-butyric acid

Ausbeute 94.0%

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was refluxed for 30 min
2. 2
   SonstigeThe solvent was evaporated under reduced pressure
3. 3
   Extraktionthe reaction mixture was extracted with ether (100×3)
4. 4
   Waschenthe combined organic phases were washed with water
5. 5
   Trocknendried over sodium sulfate and solvent
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   SonstigeThe crude product was purified by column chromatography (20:80 EtOAc:Hexanes)

Vorschrift

5.95 g of sodium hydroxide was dissolved in 200 mL of methanol in a 500 mL round bottom flask. The reaction mixture was cooled to room temperature and 55 (6.78 g, 22.90 mmol) was added followed by 20 mL of water and 100 mL of methanol and the reaction mixture was refluxed for 30 min. The solvent was evaporated under reduced pressure and the reaction mixture was neutralized with dilute hydrochloric acid and the reaction mixture was extracted with ether (100×3) and the combined organic phases were washed with water and dried over sodium sulfate and solvent evaporated under reduced pressure. The crude product was purified by column chromatography (20:80 EtOAc:Hexanes) to yield 5.43 g of 56 as tan colored solid (94%).

Quelle