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

HRID 899033

Reaction equation

HRID 899033 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>>[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

5

Reactant 4

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

Product 1

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

Procedure

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. The 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. The concentrated 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.

Workup

  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. customThe concentrated residue was recrystallized from ethyl acetate and toluene

Sources & evidence

ORD record
ord-c94738518824485999d7b144da974450
Source dataset
uspto-grants-2008_04
Patent number
US07354746B1

Linked notes

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