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

HRID 1593695Notes

Reaction equation

HRID 1593695 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 were 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 was adjusted to pH 2.2, for extraction into ethyl acetate. The organic layer was rinsed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to obtain the residue. The residue was 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 was adjusted to pH 2.2, for extraction into ethyl acetate
  3. washThe organic layer was rinsed with saturated aqueous 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
  8. customtoluene to obtain PHOG of 2.8 g (11.3 mmol.) in crystal

Sources & evidence

ORD record
ord-7fed949d612c4fdab9a8fa45dcc1678d
Source dataset
uspto-grants-2007_11
Patent number
US07297800B2

Reaction notes

Loading…