反应 #55586

反应方程式

sodium hydroxide

1,7-octadiene

Borane

hydrogen peroxide

→

title compound

Oct-7-en-1-ol

溶剂

water

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   其他was prepared under nitrogen
2. 2
   温度while maintaining the mixture at 30° to 40° C
3. 3
   其他the phases which formed
4. 4
   其他were separated
5. 5
   萃取The aqueous phase was extracted 3 times with an equal volume of pentane
6. 6
   洗涤The combined pentane extracts were washed with 200 ml of 10% aqueous sodium bisulfite
7. 7
   干燥with saturated aqueous sodium chloride and then dried over magnesium sulfate
8. 8
   过滤The mixture was filtered
9. 9
   其他the filtrate was evaporated
10. 10
    workup.DISTILLATIONdistilled

实验过程

A mixture containing 1.7 liter of anhydrous tetrahydrofuran (distilled from sodium/benzophenone ketyl) and 600 g (5.4 mol) of distilled 1,7-octadiene (Aldrich Chemical Co. Inc.) was prepared under nitrogen. Borane in tetrahydrofuran (1 M, 600 ml, 0.60 mol) was added dropwise to the mixture over a 1.0 hr period while the mixture was maintained at 25° C. The resultant solution was stirred for 1 hr at room temperature and then 25 ml of water was added thereto followed by 300 ml of 3 M sodium hydroxide. These additions were followed by 300 ml of 30% aqueous hydrogen peroxide while maintaining the mixture at 30° to 40° C. The mixture was stirred for 15 min and the phases which formed were separated. The aqueous phase was extracted 3 times with an equal volume of pentane. The combined pentane extracts were washed with 200 ml of 10% aqueous sodium bisulfite, then with saturated aqueous sodium chloride and then dried over magnesium sulfate. The mixture was filtered and the filtrate was evaporated and distilled to yield the title compound (bp 62°-64° C., 20 mm) as a colorless oil having the following physical characteristics:

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