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

Participants

Reaction Steps

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.

Provenance & Evidence