Hydrochloric Acid → HCID 23679672, compound

HRID 1086363Notes

Reaction equation

HRID 1086363 reaction equation
[OH-].[Na+:2].[O:3]=[C:4]([CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:5]([O-:7])=[O:6].[Na+].[CH3:18]I.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[O:3]=[C:4]([C:8]([CH3:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:5]([O-:7])=[O:6].[Na+:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium Hydroxide2×HCID 23679662HCID 23679662, compound

Product 1

HCID 23679672HCID 23679672, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 3N aqueous solution (0.84 ml) of sodium hydroxide and 3.0 ml of tetrahydrofuran were added to 0.30 g (1.39 mmoles) of sodium 2-oxo-3-phenylpentanoate, and the mixture was stirred until a completely uniform solution formed. Then, 0.23 mg (2.8 mmoles) of methyl iodide and 36 mg (0.16 mmole) of triethylbenzylammonium chloride were added, and the mixture reacted at room temperature for 7 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with ether. The ether layer was dried over magnesium sulfate. The drying reagent was separated by filtration, and the solvent was evaporated. The NMR spectral analysis of the resulting oily product led to the determination that the desired 2-oxo-3-methyl-3-phenylpentanoic acid formed in a yield of 62 %. Then, 1.2 ml of a 1N aqueous solution of sodium hydroxide was added to this product, and the mixture was concentrated under reduced pressure. Ether was added, and the precipitated white solid was isolated by filtration to give 0.15 g (0.63 mmole) of sodium 2-oxo-3-methyl-3-phenylpentanoate in a yield of 46 %.

Workup

  1. customformed
  2. customthe mixture reacted at room temperature for 7 hours
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried over magnesium sulfate
  5. customThe drying reagent was separated by filtration
  6. customthe solvent was evaporated
  7. customformed in a yield of 62 %
  8. concentrationthe mixture was concentrated under reduced pressure
  9. additionEther was added
  10. customthe precipitated white solid was isolated by filtration

Sources & evidence

ORD record
ord-fccbdbd267e745d4afd045f116e6afc4
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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