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

HRID 133665

Reaktionsgleichung

Reaktionsgleichung von HRID 133665
[OH-].[K+].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)[CH2:16][C:17]([C:19]([OH:21])=[O:20])=[O:18].Cl>O.C1(C)C=CC=CC=1>[CH2:9]([C:10]([OH:14])([C:11]([OH:13])=[O:12])[CH2:16][C:17](=[O:18])[C:19]([OH:21])=[O:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

After 16.23 g of potassium hydroxide (having a purity of 85% by weight) was dissolved in 48 ml of water, 5.0 g (30.5 mmol) of phenylpyruvic acid and 12.1 g (91.4 mmol) of oxalacetic acid were added to the resulting solution, for reaction at ambient temperature for 72 hours (about pH 13 at the start of the reaction). Using conc. hydrochloric acid, the reaction solution was adjusted to pH 2.2, and extracted in ethyl acetate. The organic layer was rinsed in aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated to obtain the residue. The residue was recrystallized in ethyl acetate and toluene, to obtain 2.8 g (11.3 mmol) of 4-benzyl-4-hydroxy-2-ketoglutaric acid in crystal form.

Aufarbeitung

  1. customat the start of the reaction)
  2. extractionextracted in ethyl acetate
  3. washThe organic layer was rinsed in aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain the residue
  7. customThe residue was recrystallized in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-699fd30199a843e5a8a3aecdad1280d0
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390909B2

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