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

HRID 2113410Notes

Reaction equation

HRID 2113410 reaction equation
[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>[C:3]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])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 13.8 g of potassium hydroxide (85% purity) dissolved in 25 ml of water were added 5.0 g (30.5 mmol) of phenylpyruvic acid and 12.1 g (91.4 mmol) of oxalacetic acid, and the mixture was allowed to react at room temperature for 72 hours. The reaction mixture was adjusted at pH 2.2 with conc. hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried on anhydrous magnesium sulfate, and condensed to yield a residue. This was recrystallized from ethyl acetate and toluene to yield 2.8 g (11.3 mmol) of 4-phenylmethyl-4-hydroxy-2-ketoglutaric acid as crystals.

Workup

  1. customto react at room temperature for 72 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried on anhydrous magnesium sulfate, and condensed
  5. customto yield a residue
  6. customThis was recrystallized from ethyl acetate and toluene

Sources & evidence

ORD record
ord-93f71a360ac84b909cf9a32f1cbb5674
Source dataset
uspto-grants-2008_10
Patent number
US07432100B2

Reaction notes

Loading…