Phenylpyruvic acid → Sodium 2-oxo-3-phenylbutanoate

HRID 1086340Notes

Reaction equation

HRID 1086340 reaction equation
[OH-].[Na+:2].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:15]I>O1CCCC1>[O:14]=[C:10]([CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:15])[C:11]([O-:13])=[O:12].[Na+:2]

Participants

5

Reactant 3

HCID 997Phenylpyruvic acidHCID 6328Methyl iodideHCID 14798Sodium Hydroxide

Product 1

HCID 23676252Sodium 2-oxo-3-phenylbutanoateYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous solution of sodium hydroxide (20 ml, 20 mmoles) and 30 ml of tetrahydrofuran were added to 1.64 g (10.0 mmoles) of phenylpyruvic acid to form a solution. Then, 2.0 ml of methyl iodide was added, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated, and ether was added to the resulting pale yellowish white semi-solid. The precipitated sodium 2-oxo-3-phenylbutanoate as a white solid (0.68 g, yield 68 %) was isolated by filtration.

Workup

  1. customto form a solution
  2. concentrationThe reaction mixture was concentrated
  3. additionether was added to the resulting pale yellowish white semi-solid

Sources & evidence

ORD record
ord-e00b7c8585e447fbb58d58e56489a553
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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