Phenol → {2-[(2-Methylpentan-2-yl)peroxy]propan-2-yl}benzene

Participants

Reaction Steps

Into the 200 ml jacketed reactor described in Example II were added 15.6 grams (0.13 m) alpha-methylstyrene, 15.0 grams (0.104 m) 82% t-hexyl hydroperoxide and 4.0 grams (0.043 m) phenol. The mixture was stirred to obtain a clear solution and the temperature was adjusted to 20° C. To this solution was added 1.5 grams (0.0095 m) of t-cumyl chloride from the addition funnel over 5 minutes while holding the temperature at 21°-22° C. The reaction self-exothermed to 25° C. over 10 minutes and then was stirred an additional 1/2 hour at 25° C. The reaction was then stirred 80 minutes at 35° C. and 90 minutes at 40° C. at which point the reaction was complete. The reaction was terminated by adding 25 mls of water, stirring 5 minutes, adding 5 mls of 50% NaOH, stirring another 5 minutes and separating the aqueous caustic layer. The organic layer was successively washed with 25 mls of 15% NaOH, saturated NaHCO3 solution, water, 15% NaHSO3 solution, saturated NaHCO3 solution and water. After drying with anhydrous sodium sulfate the crude product weighed 26.7 grams and contained 80.6% cumyl t-hexyl peroxide for a corrected yield of 21.5 grams and a 87.8% yield. The pure cumyl t-hexyl peroxide was isolated by fractional distillation under vacuum.

Provenance & Evidence