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 528 g of 1,3-dichloro-2-propanol, 6.6 g of BF3 dihydrate, and 103 g of 1-dodecene at room temperature. The mixture is heated to 95° C. for 6 hours. The reaction mixture is cooled to room temperature and is then transferred to a 1000 ml separation funnel; 200 ml of heptane is added and two phases are separated. The lower phase (containing 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 the heptane is removed on a rotary evaporator. Distillation of residual heptane under reduced pressure affords 46.3 g of dodecene isomers mixture and 94.4 g of sec-dodecyl 1,3-dichloro-2-propyl ether and isomers. The dodecene mixtures is collected at 80-105° C./0.6 mmHg, and the ether product is collected as 128-141° C./0.6 mmHg)

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. customis then transferred to a 1000 ml separation funnel
4. addition200 ml of heptane is added
5. customtwo phases are separated
6. additionThe lower phase (containing excess dichloropropanol, ether products
7. extractionunreacted and isomerized olefins, and the catalyst) is extracted with 200 ml of heptane three more times
8. customthe heptane is removed on a rotary evaporator
9. distillationDistillation of residual heptane under reduced pressure

ORD record

ord-e3f17a5f5b064a1ea44ce4f72ea54fd8

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722944B2