Réaction #586114

Équation de réaction

3-bromophenol

aluminum chloride

2,5-dichloro-2,5-dimethylhexane

→

3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-1-ol

Rendement 68.0%

Solvants

ethyl ether

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONafter which it is poured onto ice
2. 2
   Extractionextracted with dichloromethane
3. 3
   AutreThe residue obtained
4. 4
   Lavagethis organic phase is then washed with 1N sodium hydroxide solution
5. 5
   AutreThe residue obtained
6. 6
   Autreis purified by chromatography (eluent
7. 7
   AutreA thick oil is obtained (67 g; yield=68%)

Mode opératoire

60 g (347 mmol) of 3-bromophenol are dissolved in 600 mL of dichloromethane. This solution is added to a solution of 46 g (347 mmol) of aluminum chloride in 200 mL of dichloromethane. 127 g (694 mmol) of 2,5-dichloro-2,5-dimethylhexane are added in 10 g portions every 40 minutes. The medium is then stirred for 10 hours, after which it is poured onto ice and extracted with dichloromethane. The residue obtained is dissolved in ethyl ether and this organic phase is then washed with 1N sodium hydroxide solution, and then with water. The residue obtained is purified by chromatography (eluent:heptane and then 1/1 heptane/dichloromethane). A thick oil is obtained (67 g; yield=68%).

Source