Reaktion #54158

Reaktionsgleichung

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

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a one litre reaction vessel
2. 2
   Sonstigeequipped with a stirrer
3. 3
   Sonstigethe reaction
4. 4
   workup.ADDITIONwas added in four hours
5. 5
   Sonstigeat 35°-40° C
6. 6
   SonstigeThe layers were separated
7. 7
   Extraktionthe water layer extracted twice with toluene
8. 8
   WaschenThe combined organic layers were washed with 5% soda solution until alkaline and subsequently with water until neutral
9. 9
   SonstigeThe 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
    Sonstigeboiling between 93° and 95° C.
12. 12
    Sonstigewas collected

Vorschrift

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.

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