Ibuprofen, (+-)- → Ibuprofen, Sodium Salt

Participants

Reaction Conditions

Reaction Steps

A portion of the enol-acetate solution (V) from A above, (55.41 g. representing 49.3 mmole of enol-acetate) was placed in a 250 ml. 1 necked flask and stirred magnetically while 10 ml. of saturated sodium chloride solution and 16.0 g. of 50 percent sodium hydroxide (200 meq.) were added. The mixture was stirred and allowed to cool to 25° C. and the ammonium persulfate [(NH4)2S2O8 ] (12.5 g.; 55 meq.) in 16 ml. of water were added over 10 minutes. After stirring overnight, 10 ml. of diglyme was added and the pH was adjusted from 9 to 13. The mixture was slowly cooled to 0° C. with seeding with crystals of 2-(4'-isobutylphenyl)propionic acid, sodium salt and held at 0° C. for 3 hours to form solid sodium 2-(4'-isobutylphenyl)propionate (VI) as a crystalline precipitate.

Provenance & Evidence