Reaction #2200592

Reaction equation

hydrochloric acid

phenylpyruvic acid

oxalacetic acid

potassium hydroxide

→

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

Yield 37.0%

Solvents

water

Conditions

Workup

1. 1
   Otherto react at room temperature for 72 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe organic layer was washed with saturated brine
4. 4
   Dryingdried on anhydrous magnesium sulfate, and condensed
5. 5
   Otherto yield a residue
6. 6
   OtherThis was recrystallized from ethyl acetate and toluene

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.

Source