Water → 1-Bromo-6-methoxyhexane

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.

1. waitthe reaction mixture was held an additional hour
2. washthe organic phase was washed with brine
3. dry with materialdried with magnesium sulfate
4. filtrationfiltered
5. distillationFractional distillation under vacuum

ORD record

ord-01faa00a5ee743848313ef65f3dfd14c

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06365549B2