Hydrochloric Acid → Sodium 2-oxo-3-phenylbutanoate

HRID 1086339Notes

Reaction equation

HRID 1086339 reaction equation
[OH-].[Na+:2].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na+].[CH3:16]I.Cl>CO>[O:14]=[C:10]([CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:16])[C:11]([O-:13])=[O:12].[Na+:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium Hydroxide2×HCID 23667645Sodium phenylpyruvate

Product 1

HCID 23676252Sodium 2-oxo-3-phenylbutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2N aqueous solution of sodium hydroxide (10 ml, 20 mmoles) and 30 ml of methanol were added to 3.92 g (20 mmoles) of sodium phenylpyruvate to form a solution. Then, 1.25 ml of methyl iodide was added, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with 150 ml of ether. The ether layer was dried over magnesium sulfate, and concentrated under reduced pressure to give a pale yellowish white oil. A 3N aqueous solution of sodium hydroxide (6.5 ml) was added, and the mixture was concentrated. Ether was added to the resulting semi-solid mixture, and the precipitated sodium 2-oxo-3-phenylbutanoate was isolated by filtration as a white solid (1.62 g, yield 85 %).

Workup

  1. customto form a solution
  2. extractionextracted with 150 ml of ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a pale yellowish white oil
  6. concentrationthe mixture was concentrated
  7. additionEther was added to the resulting semi-solid mixture

Sources & evidence

ORD record
ord-9088c69b4e8d4176a43a3a75d6754416
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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