Reaction #640559

Reaction equation

Phenyl pyruvic acid

oxaloacetic acid

potassium hydroxide

hydrochloric acid

→

4-phenylmethyl-4-hydroxy-2-ketoglutaric acid

Yield 37.0%

Conditions

Workup

1. 1
   workup.DISSOLUTIONhad been dissolved
2. 2
   Otherreacted at room temperature for 72 hours
3. 3
   Extractionthe reaction mixture was extracted with ethyl acetate
4. 4
   WashAn organic layer was washed with saturated aqueous NaCl solution
5. 5
   Otherdried on magnesium sulfate anhydrate
6. 6
   Concentrationconcentrated
7. 7
   Otherto yield residue
8. 8
   OtherThe residue was recrystallized from ethyl acetate and toluene

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. A 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 to yield residue. The 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.

Source