反応 #54158

反応方程式

magnesium

tetrahydrofurane

allyl chloride

allyl chloride

tetrahydrofurane

tricyclo [5,2,1,02,6 ] decan-8-one

→

8-allyl-8-hydroxytricyclo [5,2,1,02,6 ] decane

溶媒

acetic acid

反応条件

後処理

1. 1
   その他In a one litre reaction vessel
2. 2
   その他equipped with a stirrer
3. 3
   その他the reaction
4. 4
   workup.ADDITIONwas added in four hours
5. 5
   その他at 35°-40° C
6. 6
   その他The layers were separated
7. 7
   抽出the water layer extracted twice with toluene
8. 8
   洗浄The combined organic layers were washed with 5% soda solution until alkaline and subsequently with water until neutral
9. 9
   その他The organic solvent was removed by distillation under reduced pressure
10. 10
    workup.DISTILLATIONThe residue was distilled on a Vigreux head at 2 mm.Hg
11. 11
    その他boiling between 93° and 95° C.
12. 12
    その他was collected

実験手順

In a one litre reaction vessel, equipped with a stirrer, a cooler and a dropping funnel, 26.4 g magnesium, 100 g tetrahydrofurane and 1 g allyl chloride were heated to about 40° C. to start the reaction. A mixture of 76.5 g allyl chloride, 250 g tetrahydrofurane and 150 g tricyclo [5,2,1,02,6 ] decan-8-one was added in four hours, keeping the temperature at 35°-40° C. The reaction mixture was stirred for an additional 30 minutes and subsequently poured into a mixture of 600 g of ice and 80 g of acetic acid. The layers were separated and the water layer extracted twice with toluene. The combined organic layers were washed with 5% soda solution until alkaline and subsequently with water until neutral. The organic solvent was removed by distillation under reduced pressure. The residue was distilled on a Vigreux head at 2 mm.Hg. The fraction boiling between 93° and 95° C. was collected.

出典