1,3-Dichloro-2-propanol → 1-Dodecene

Temperature

95 °C

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).

1. customTo a 1000 ml round bottom flask equipped with condenser, overhead stirrer, and nitrogen inlet system
2. temperatureThe reaction mixture is cooled to room temperature
3. customtransferred to a 1000 ml separation funnel
4. addition200 ml of heptane is added
5. customtwo phases are separated
6. additionThe lower phase containing the excess dichloropropanol, ether products
7. extractionunreacted and isomerized olefins, and the catalyst is extracted with 200 ml of heptane three more times
8. customheptane is removed on a rotary evaporator
9. distillationDistillation under reduced pressure

ORD record

ord-9b4cd9a547224da7b4ccba5fb460dac0

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722944B2