Hydrochloric Acid → HCID 12218047, compound

HRID 1086341Notes

Reaction equation

HRID 1086341 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]>CN(C)C=O>[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 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1N aqueous solution of sodium hydroxide (20 ml, 20 mmoles) and 30 ml of dimethylformamide 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 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 solid. Analysis of its NMR spectrum showed that 2-oxo-3-phenylbutanoic acid formed in a yield of 59%, and 2-oxo-3-methyl-3-phenylbutanoic acid, in a yield of 21%. The NMR spectrum of the former is shown in Example 1, and that of the latter is shown in Example 73.

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 solid

Sources & evidence

ORD record
ord-fde864653b40408685b916085e9df722
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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