Reaction #927244

Reaction equation

Hexane

water

1,6-dibromohexane

sodium methoxide

1,6-dibromohexane

sodium methoxide

→

6-bromohexyl methyl ether

Yield 93.0%

Solvents

methanol

Conditions

Workup

1. 1
   workup.WAITthe reaction mixture was held an additional hour
2. 2
   Washthe organic phase was washed with brine
3. 3
   Dryingdried with magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   workup.DISTILLATIONFractional distillation under vacuum

Procedure

6-Bromohexyl methyl ether was prepared from 1,6-dibromohexane. To 48.8 g (200 mmol) of 1,6-dibromohexane at 60° C. was added 44 g (200 mmol) of a 25% solution of sodium methoxide in methanol. The reaction mixture was held 0.5 hours, then an additional 4 g of sodium methoxide solution was added, and the reaction mixture was held an additional hour. Hexane and water were added, the organic phase was washed with brine and dried with magnesium sulfate, filtered and stripped. Fractional distillation under vacuum gave 93% pure 6-bromohexyl methyl ether. This bromide was converted to the Grignard reagent, which was converted to 1-(7-methoxyheptyl)-cyclopropene in the same manner that pentylmagnesium bromide was converted to 1-hexylcyclopropene.

Source