Ethanol → 4-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acid

HRID 1166639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166639
C([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[CH:11]=1)([CH3:9])[CH3:8])C.C(O)C.[OH-].[K+]>O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]([CH3:8])([CH3:9])[CH2:6][CH2:5][C:4]([OH:19])=[O:3])=[CH:11][C:12]=1[CH3:18]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21024370HCID 21024370, Verbindung2×

Produkt 1

HCID 222183274-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-(4-methoxy-3-methylphenyl)-4-methyl-pentanoic acid ethyl ester (Compound 4, 6.8 g, 25.8 mmol) and 20 mL of absolute ethyl alcohol was added aqueous 5M KOH (6 mL). The resulting solution was heated in an 60° C. bath for 24 h. The solution was cooled to room temperature, diluted with water and washed once with 2:1 hexane:ethyl acetate solution, and the layers were separated. The aqueous layer was acidified with HCl 2N to pH=0-1 and the product extracted three times with ethyl acetate. The combined organic extracts were washed with brine, and dried over MgSO4, and filtered. The solvent was removed to give 5.9 g (97%) of the title compound as a dark oil.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. washwashed once with 2:1 hexane
  3. customethyl acetate solution, and the layers were separated
  4. extractionthe product extracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-c0db8e68053d4a929d4422e92a3677d6
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613917B1

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