tert-Butyl hydroperoxide → HCID 20367908, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of 9.1 grams (.0407 moles) of 25% potassium hydroxide solution in a 100 ml. reaction flask equipped with a magnetic stirrer, thermometer and addition funnel was added 5.2 grams (.052 moles) of 90% t-butyl hydroperoxide. The reaction mixture was stirred for 30 minutes at 25° C and then cooled to 18° C. To the above solution was added 8.06 grams (0.037 moles) of 2-t-amylazo-2-chloro-4-methylpentane dropwise over 15 minutes holding the temperature at 18°-22° C with a cold water bath. After the addition was complete, the reaction was stirred for 10 minutes at 20° C, cooled to 5° C and stirred an additional 40 minutes. A small portion of 50% sodium hydroxide was then added to react with the excess t-butyl hydroperoxide and the reaction stirred for an additional 15 minutes, poured into 150 ml. of ice cold water and the product extracted with pentane. The pentane solution was washed with ice cold water, saturated NaHCO3 solution and water. The pentane solution was dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 8.3 grams (83% yield) of crude 2-t-amylazo-2-(t-butylperoxy)-4-methylpentane.

Provenance & Evidence