Reacción #586114

Ecuación de reacción

3-bromophenol

aluminum chloride

2,5-dichloro-2,5-dimethylhexane

→

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

Rendimiento 68.0%

Disolventes

ethyl ether

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente