Hydrochloric Acid → HCID 23676255, compound

Participants

Reaction Steps

A 3N aqueous solution of sodium hydroxide (4.0 ml, 12 mmoles) and 10 ml of methanol were added to 0.53 g (3.0 mmoles) of p-methylphenylpyruvic acid to form a solution. Then, 1.0 ml of methyl iodide was added, and the mixture was stirred at room temperature for 4.5 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with three 30 ml portions of ether. The ether layers were dried over magnesium sulfate, and concentrated under reduced pressure to give a pale brown oil. Its NMR spectral analysis led to the determination that 2-oxo-3-(p-methylphenyl)butanoic acid was formed in a yield of 80 %. To this product was added 3 ml of a 3N aqueous solution of sodium hydroxide, and the mixture was concentrated under reduced pressure. Ether was added to the resulting semi-solid mixture, and the precipitated sodium 2-oxo-3-(p-methylphenyl)butanoate was isolated by filtration as a white solid.

Provenance & Evidence