1,3-Dichloro-2-propanol → 1-Dodecene

Participants

Reaction Conditions

Reaction Steps

To a 1000 ml round bottom flask equipped with condenser, overhead stirrer, and nitrogen inlet system is added 526.2 g of 1,3-dichloro-2-propanol, 7.8 ml of boron trifluoride diethyl etherate, and 101 g of 1-dodecene at room temperature. The mixture is heated to 95° C. for 1 hour. The reaction mixture is cooled to room temperature and then transferred to a 1000 ml separation funnel. 200 ml of heptane is added and two phases are separated. The lower phase containing the excess dichloropropanol, ether products, unreacted and isomerized olefins, and the catalyst is extracted with 200 ml of heptane three more times. The heptane solutions are combined and heptane is removed on a rotary evaporator. Distillation under reduced pressure affords 46.3 g of dodecene isomers mixture and 91.6 g of sec-dodecyl 1,3-dichloro-2-propyl ether and isomers. Yield=51.3% (based on 1-dodecene).

Provenance & Evidence