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

HRID 219511

Reaction equation

HRID 219511 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-04a67da8c5fa46e0be4146d765739251
Source dataset
uspto-grants-2012_06
Patent number
US08202711B2

Linked notes

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