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

HRID 553377

Reaktionsgleichung

Reaktionsgleichung von HRID 553377
[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>>[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

5

Edukt 4

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

Produkt 1

HCID 101714744-Benzyl-4-hydroxy-2-ketoglutaric acidAusbeute 37 %

Versuchsvorschrift

Phenyl pyruvic acid (5.0 g, 30.5 mmol) and 12.1 g (91.4 mmol) of oxaloacetic acid were added to 25 mL of aqueous solution in which 13.8 g of potassium hydroxide (purity 85%) had been dissolved, and reacted at room temperature for 72 hours. A pH value of the reaction mixture was adjusted to 2.2 using concentrated hydrochloric acid, and the reaction mixture was extracted with ethyl acetate. An organic layer was washed with saturated aqueous NaCl solution, dried on magnesium sulfate anhydrate, and then concentrated to yield residue. The residue was recrystallized from ethyl acetate and toluene to yield 2.8 g (11.3 mmol) of 4-phenylmethyl-4-hydroxy-2-ketoglutaric acid as crystal.

Aufarbeitung

  1. dissolutionhad been dissolved
  2. customreacted at room temperature for 72 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washAn organic layer was washed with saturated aqueous NaCl solution
  5. customdried on magnesium sulfate anhydrate
  6. concentrationconcentrated
  7. customto yield residue
  8. customThe residue was recrystallized from ethyl acetate and toluene

Quellen und Nachweise

ORD-Eintrag
ord-7a195b115e354b77a085f722371f1b31
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048647B2

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