反应 #502076

反应方程式

3,7-dimethyloct-6-en-3-ol

Sodium hydride

allyl bromide

→

6-(allyloxy)-2,6-dimethyloct-2-ene

溶剂

dimethylformamide

反应条件

后处理

1. 1
   其他fitted with thermocouple, condenser and addition funnel
2. 2
   其他To the stirred reaction mixture
3. 3
   温度cooled to ice bath temperature
4. 4
   温度whilst maintaining
5. 5
   温度cooling
6. 6
   workup.ADDITIONwas added to the reaction mixture
7. 7
   萃取extracted with methyltert-butyl ether (3×30 mL)
8. 8
   洗涤The combined organic phase was washed with dilute hydrochloric acid (100 mL), saturated brine (100 mL)
9. 9
   干燥dried with magnesium sulphate
10. 10
    其他The solvent was removed in vacuo
11. 11
    workup.DISTILLATIONthe residue fractionally distilled

实验过程

Sodium hydride (60% dispersion in mineral oil, 6.8 g, 170 mmol) and dimethylformamide (100 mL) were added to a three necked 500 mL flask fitted with thermocouple, condenser and addition funnel. To the stirred reaction mixture was added dropwise 3,7-dimethyloct-6-en-3-ol (22 g, 139 mmol) at room temperature. The mixture was stirred for 1 hr, cooled to ice bath temperature then allyl bromide (97% pure by GC RPA, 19 g, 15 mmol) was added dropwise whilst maintaining cooling. After a further 3 hr stirring ice/water was added to the reaction mixture and then extracted with methyltert-butyl ether (3×30 mL). The combined organic phase was washed with dilute hydrochloric acid (100 mL), saturated brine (100 mL) and dried with magnesium sulphate. The solvent was removed in vacuo and the residue fractionally distilled to give 6-(allyloxy)-2,6-dimethyloct-2-ene (25.4 g, 92% pure by GC RPA, 118 mmol, chemical yield 70%).

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