Hydrochloric Acid → HCID 12225940, compound

HRID 1086351Notes

Reaction equation

HRID 1086351 reaction equation
[OH-].[Na+].[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:18])[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)[CH:4]([CH3:6])[CH3:5].Cl.[CH3:20]I>>[O:18]=[C:14]([CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:3][CH:4]([CH3:6])[CH3:5])=[CH:8][CH:9]=1)[CH3:20])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 15023986HCID 15023986, compound

Product 1

HCID 12225940HCID 12225940, compoundYield 67%

Procedure

A 3N aqueous solution of sodium hydroxide (20 ml; 60 mmoles) was slowly added to a solution of 6.60 g (30 mmoles) of p-isobutylphenylpyruvic acid and 10 ml of methyl iodide. After the addition, the mixture was stirred at room temperature for 4 hours, acidified with 1N hydrochloric acid, and extracted with 150 ml of ether. The ether layer was dried over magnesium sulfate, and the ether was evaporated under reduced pres-sure to give pale yellowish white crystals. The NMR spectrum of the crystals led to the determination that the crystals were nearly pure 2-oxo-3-(p-isobutylphenyl)butanoic acid (4.67 g; yield 67 %).

Workup

  1. additionAfter the addition
  2. extractionextracted with 150 ml of ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. customthe ether was evaporated under reduced pres-sure
  5. customto give pale yellowish white crystals

Sources & evidence

ORD record
ord-6565b67045204b00a003f904b573db04
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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