Reaction #586114

Reaction equation

3-bromophenol

aluminum chloride

2,5-dichloro-2,5-dimethylhexane

→

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

Yield 68.0%

Solvents

ethyl ether

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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