Hydrogen Peroxide → 3,3-Dimethyl-5-oxohexanoic acid

Participants

Reaction Conditions

Reaction Steps

Isophorone (138 g) and 30% hydrogen peroxide (730 g) are dissolved in isopropanol (500 ml), and the solution is cooled to 15° C. 3N Sodium hydroxide solution (800 ml) is added slowly over a three-hour period to maintain the temperature of the reaction below 20° C. by adjusting the addition rate of sodium hydroxide solution and cooling with an ice-water bath. The reaction is allowed to warm to ambient temperature while stirring for 16 hours. The reaction mixture is extracted once with isopropyl ether (200 ml) then treated with sodium bisulfite (40 g) and acidified to pH 2 with concentrated hydrochloric acid (225 ml). The solution is extracted twice with methylene chloride (200 ml) and the resulting methylene chloride solution stripped under vacuum at 40° C., 10 mm Hg to give 3,3-dimethyl-5-ketohexanoic acid as a residue product.

Provenance & Evidence