Reaktion #220162

Reaktionsgleichung

ethyl aluminium dichloride

1-(3′,3′-dimethylcyclohexyl)ethanol

isobutylenoxide

→

2-[1′-(3″,3″-dimethylcyclohexyl)-ethoxy]-2-methylpropan-1-ol

Ausbeute 38.0%

Lösungsmittel

toluene

cyclohexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   Sonstigethe cooling bath was removed
3. 3
   workup.ADDITIONThe reaction mixture was then poured into 1 L of brine
4. 4
   Extraktionextracted with ether
5. 5
   WaschenThe combined organic extracts were washed with brine and water
6. 6
   Trocknendried with sodium sulphate
7. 7
   Einengenconcentrated on a rotary evaporator
8. 8
   workup.DISTILLATIONDistillation of the crude material (136 g)

Vorschrift

At 0° C. under an atmosphere of nitrogen, 178 ml (321 mmol) of a 1.8 M solution of ethyl aluminium dichloride in toluene was slowly added to a stirred solution of 100 g (641 mmol) of 1-(3′,3′-dimethylcyclohexyl)ethanol and 55.4 g (769 mmol) of isobutylenoxide in 500 ml of cyclohexane. After complete addition, the cooling bath was removed, the reaction mixture was allowed to warm to room temperature, and stirring was continued at this temperature for 15 h. The reaction mixture was then poured into 1 L of brine, acidified with concentrated phosphoric acid, and thrice extracted with ether. The combined organic extracts were washed with brine and water, dried with sodium sulphate, and concentrated on a rotary evaporator. Distillation of the crude material (136 g) provided at 78-85° C./0.3 mbar 55.1 g (38%) of pure 2-[1′-(3″,3″-dimethylcyclohexyl)-ethoxy]-2-methylpropan-1-ol, while 60.4 g of starting material were recovered.

Quelle