Water → (+)-4-Hydroxy-4'-(2-methylbutanoyl) biphenyl

HRID 846556

Reaktionsgleichung

Reaktionsgleichung von HRID 846556
CC(CC)C(O)=[O:4].[CH3:8][CH:9]([CH2:24][CH3:25])[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11].O.C(=O)([O-])O.[Na+]>CO>[OH:4][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH:9]([CH3:8])[CH2:24][CH3:25])=[CH:13][CH:14]=2)=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 679137652-Methylbutanoic acid 4-(2-methylbutanoyl) biphenyl

Produkt 1

HCID 14745904(+)-4-Hydroxy-4'-(2-methylbutanoyl) biphenylAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

0.67 g of the above 2-methylbutanoic acid-4-(2-methylbutanoyl) biphenyl was mixed with 95 ml of methyl alcohol and 5 ml of water and added with 1.14 g (13.6 mmol) of sodium hydrogen carbonate with stirring, which was subjected to hydrolysis reaction at room temperature for 40 hours. After the completion of the reaction, methanol was distilled off and 1 normal hydrochloric acid was added to adjust pH to not more than 1, and the extraction with dichloromethane was performed. The extracted liquid was washed with water, dried on anhydrous sodium sulfate and purified by a column chromatography of silica gel after the removal of the solvent to obtain 0.44 g (yield 88%) of (+)-4-hydroxy-4'-(2-methylbutanoyl) biphenyl at a light yellow crystal having the aforementioned properties.

Aufarbeitung

  1. customwhich was subjected to hydrolysis reaction at room temperature for 40 hours
  2. distillationwas distilled off
  3. addition1 normal hydrochloric acid was added
  4. extractionthe extraction with dichloromethane
  5. washThe extracted liquid was washed with water
  6. dry with materialdried on anhydrous sodium sulfate
  7. custompurified by a column chromatography of silica gel
  8. customafter the removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-4b8fb10e80624a48ad53c387e8cec10a
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137653

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