반응 #640559

ord-7a195b115e354b77a085f722371f1b31

반응 방정식

O=C(O)C(=O)Cc1ccccc1
Phenyl pyruvic acid
O=C(O)CC(=O)C(=O)O
oxaloacetic acid
[K+].[OH-]
potassium hydroxide
Cl
hydrochloric acid
O=C(O)C(=O)CC(O)(Cc1ccccc1)C(=O)O
4-phenylmethyl-4-hydroxy-2-ketoglutaric acid
수율 37.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.DISSOLUTIONhad been dissolved
  2. 2
    기타reacted at room temperature for 72 hours
  3. 3
    추출the reaction mixture was extracted with ethyl acetate
  4. 4
    세척An organic layer was washed with saturated aqueous NaCl solution
  5. 5
    기타dried on magnesium sulfate anhydrate
  6. 6
    농축concentrated
  7. 7
    기타to yield residue
  8. 8
    기타The residue was recrystallized from ethyl acetate and toluene

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08048647B2uspto-grants-2011_11