Pyridine → 11-Chloro-1-undecene

Temperature

50 °C

A one liter, three necked flask equipped with mechanical stirrer, reflux condenser, argon inlet and addition funnel was heated in an oil bath at 50° C. To the flask was added methylene chloride (400 milliliters), undecylenol (100 grams) and pyridine (55.7 grams). Thionyl chloride (78.9 grams) in methylene chloride (100 milliliters) was added dropwise under reflux over five hours. The mixture was filtered, the solvent was removed from the filtrate using a rotary evaporator, and the resultant oil was refiltered and then distilled using a packed column to yield two fractions. A fraction collected between 100° and 110° C. and about 1 millimeter of mercury was redistilled to yield 40 grams of undecylenyl chloride as an oil obtained at 80° to 85° C. at about 1 millimeter of mercury.

1. customA one liter, three necked flask equipped with mechanical stirrer
2. temperaturereflux
3. additioncondenser, argon inlet and addition funnel
4. temperatureunder reflux over five hours
5. filtrationThe mixture was filtered
6. customthe solvent was removed from the filtrate
7. customa rotary evaporator
8. distillationdistilled
9. customto yield two fractions
10. customA fraction collected between 100° and 110° C.
11. distillationabout 1 millimeter of mercury was redistilled

ORD record

ord-548ab59572f641fdad4b393590ea8dc7

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166026