Hydrochloric Acid → HCID 12218047, compound

HRID 1086342Notes

Reaction equation

HRID 1086342 reaction equation
[OH-].[Na+].[C:3]1(CC(=O)C(O)=O)C=CC=CC=1.CI.Cl.[O:18]=[C:19]([CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])[C:20]([OH:22])=[O:21]>C(O)(C)(C)C>[O:18]=[C:19]([C:23]([CH3:3])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 997Phenylpyruvic acidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13065771HCID 13065771, compound

Product 1

HCID 12218047HCID 12218047, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A 3N aqueous solution of sodium hydroxide (3.0 ml, 9.0 mmoles) and 6 ml of t-butyl alcohol were added to 0.492 g (3.0 mmoles) of phenylpyruvic acid to form a solution. Then, 0.6 ml of methyl iodide was added, and the mixture was stirred at room temperature for 9 hours. The reaction mixture was acidified with 20 ml of 1N hydrochloric acid, and extracted with ether. The organic layer was dried over magnesium sulfate. The drying reagent was separated by filtration, and the solvent was evaporated under reduced pressure to give a pale while oil. The NMR spectral analysis of the product led to the determination that 2-oxo-3-phenylbutanoic acid was formed in a yield of 57 %, and 2-oxo-3-methyl-3phenylbutanoic acid, in a yield of 30 %.

Workup

  1. customto form a solution
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customThe drying reagent was separated by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customto give a pale while oil

Sources & evidence

ORD record
ord-5f3cb168803049b9aac9360a6bd45693
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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