Hydrochloric Acid → HCID 15024036, compound

Participants

Reaction Steps

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 %.

Provenance & Evidence