Réaction #220162

Équation de réaction

ethyl aluminium dichloride

1-(3′,3′-dimethylcyclohexyl)ethanol

isobutylenoxide

→

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

Rendement 38.0%

Solvants

toluene

cyclohexane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source