Hydrochloric Acid → 4-Benzyl-4-hydroxy-2-ketoglutaric acid

HRID 41851

Reaktionsgleichung

Reaktionsgleichung von HRID 41851
[C:1]1([CH2:7][C:8](=[O:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([CH2:18]C(O)=O)([C:15]([OH:17])=[O:16])=[O:14].[OH-].[K+].Cl>O>[C:1]1([CH2:7][C:8]([OH:12])([C:9]([OH:11])=[O:10])[CH2:18][C:13](=[O:14])[C:15]([OH:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 970Oxaloacetic AcidHCID 997Phenylpyruvic acidHCID 14797Potassium Hydroxide

Produkt 1

HCID 101714744-Benzyl-4-hydroxy-2-ketoglutaric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5.0 g (30.5 mmol) of phenylpyruvic acid and 12.1 g (91.4 mmol) of oxaloacetic acid are added to 25 ml of water preliminarily dissolving 13.8 g of potassium hydroxide (purity of 85%) therein, for reaction at ambient temperature for 72 hours. Using the conc. hydrochloric acid, the reaction solution is adjusted to pH 2.2, for extraction into ethyl acetate. The organic layer is rinsed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to obtain the residue. The residue is recrystallized in ethyl acetate and toluene to obtain PHOG of 2.8 g (11.3 mmoL) in crystal.

Aufarbeitung

  1. customfor reaction at ambient temperature for 72 hours
  2. extractionthe reaction solution is adjusted to pH 2.2, for extraction into ethyl acetate
  3. washThe organic layer is rinsed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain the residue
  7. customThe residue is recrystallized in ethyl acetate
  8. customtoluene to obtain PHOG of 2.8 g (11.3 mmoL) in crystal

Quellen und Nachweise

ORD-Eintrag
ord-0653ba4abb8e48a19c341f16c1d781ea
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08535920B2

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