Epoxidation of Z -methyl styrene

A solution was prepared by mixing an aqueous solution of sodium hydrogenphosphate (0.05 M, 5mL) and a solution prepared with concentrated 

A 100 mL flask was filled with Jacobsen s catalyst (26 mg), (Z)-methyl styrene (lmmol) and dichloromethane (1 mL). The solution was cooled with an ice-bath. To this solution was added the cold solution of bleach previously prepared (3.5 mL). 

After 5 minutes the cooling bath was removed and the two-phase reaction mixture was stirred at room temperature. The reaction was monitored by TLC (eluent petroleum ether-diethyl ether, 8 2). (Z)-Methyl styrene was UV active, R 0.85. The epoxide visualized withp-anisaldehyde dip stained yellow, R 0.63. 

After 2 hours the reaction was quenched. The reaction mixture was transferred into a 100 mL beaker, w-hexane (10 mL) was added and stirred for 10 minutes. 

The mixture was transferred into a separating funnel. The lower aqueous phase was separated and extracted with u-hexane (4 x 20 mL). The brown combined organic layers were washed with water (3 x 30 mL) and twice with brine (2 x 30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure, giving a brown oil (180 mg). 

---