반응 #54455

반응 방정식

2,2,6-trimethylcyclohexanone

3-hydroxy-3,7-dimethyl-nona-4,6,8-trien-1-yne

ammonium chloride

ethyl bromide

magnesium

→

7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

용매

benzene

benzene

diethyl ether

ether

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도to reflux for 30 minutes
3. 3
   온도the mixture refluxed 30 minutes
4. 4
   온도the mixture refluxed for 15 minutes
5. 5
   세척The organic phase was washed with brine
6. 6
   기타dried
7. 7
   농축concentrated

실험 절차

A solution of ethyl bromide (1.75 g.) in diethyl ether was added to a suspension of magnesium (0.385 g.) in ether and the mixture was heated to reflux for 30 minutes. A solution of the alcohol, 3-hydroxy-3,7-dimethyl-nona-4,6,8-trien-1-yne, (1.0 g.) in dry benzene was added and the mixture refluxed 30 minutes. A solution of 2,2,6-trimethylcyclohexanone (1.12 g.) in benzene was added and the mixture refluxed for 15 minutes and poured into saturated aqueous ammonium chloride solution. The organic phase was washed with brine dried and concentrated to give 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne which was chromatographed on activity III alumina to give pure 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethyl-cyclohexyl)-nona-1,3,5-trien-8-yne.

출처