Hydrochloric Acid → HCID 15024036, compound

HRID 1086362Notes

Reaction equation

HRID 1086362 reaction equation
[OH-].[Na+].[O:3]=[C:4]([CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)[CH3:9])[C:5]([OH:7])=[O:6].CI.Cl.[N+](=[CH2:24])=[N-]>O1CCCC1>[O:3]=[C:4]([C:8]([CH3:24])([C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)[CH3:9])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 9550DiazomethaneHCID 14798Sodium HydroxideHCID 15023993HCID 15023993, compound

Product 1

HCID 15024036HCID 15024036, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2N aqueous solution (30 ml) of sodium hydroxide and 50 ml of tetrahydrofuran were added to 2.22 g (10 mmoles) of 2-oxo-3-(p-carboxyphenyl)butanoic acid, and the mixture was stirred until a completely uniform solution formed. Then, 1.5 ml (24 mmoles) of methyl iodide was added, and the mixture reacted at room temperature for 24 hours. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with ether. The ether layer was dried. 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-phenylbutanoic acid formed in a yield of 80 %. This product was converted to a methyl ester by using diazomethane, and isolated and purified by silica gel column chromatography (ethyl acetate:hexane=1:10). Then a 1N aqueous solution of sodium hydroxide was added and the ester was hydrolyzed. The hydrolyzate was acidified with 1N hydrochloric acid and extracted with ether. After drying, the solvent was evaporated to give 0.80 g (3.4 mmoles) of 2-oxo-3-methyl-3-(p-carboxyphenyl)butanoic acid as a white solid in a yield of 34 %.

Workup

  1. customformed
  2. customthe mixture reacted at room temperature for 24 hours
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried
  5. customThe drying reagent was separated by filtration
  6. customthe solvent was evaporated
  7. customformed in a yield of 80 %
  8. customisolated
  9. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:10)
  10. additionThen a 1N aqueous solution of sodium hydroxide was added
  11. extractionextracted with ether
  12. customAfter drying
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5f822606b38e40c6b66010e9b8424bbd
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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