Reaction #927255

Reaction equation

hexane

sodium hydroxide

hexanol

2,3-dibromopropene

→

2-bromo-3-hexyloxypropene

Yield 95.0%

Solvents

water

Conditions

Workup

1. 1
   OtherTo a three neck round bottom flask equipped with an addition funnel and an overhead stirrer
2. 2
   Otherwere fed to the well-stirred reaction mixture over a 20 minute period
3. 3
   Otherthe phases were separated
4. 4
   WashThe organic phase was washed with water and brine
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   workup.DISTILLATIONThe product was fractionally distilled under reduced pressure

Procedure

To a three neck round bottom flask equipped with an addition funnel and an overhead stirrer was added 35 ml of hexane, 42 g of 50% sodium hydroxide and 0.50 g of tetra-n-butylammonium bromide. A mixture of 6.74 g of hexanol (66 mmol) and 20 g (100 mmol) of 2,3-dibromopropene were fed to the well-stirred reaction mixture over a 20 minute period. The reaction was stirred an additional 1 hour, then water was added, and the phases were separated. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and stripped. The product was fractionally distilled under reduced pressure to give 6.1 g of 95% pure 2-bromo-3-hexyloxypropene.

Source