Reaction #545887

Reaction equation

aluminum trichloride

dichloromethane

2,5-dichloro-2,5-dimethylhexane

phenol

→

title compound

Yield 90.8%

5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthol

Yield 90.8%

Solvents

methane dichloride

Conditions

Workup

1. 1
   TemperatureAfter cooled
2. 2
   Extractionextracted with ether (3×80 ml)
3. 3
   WashThe organic phase is washed with 10% NaHCO3 solution (2×150 ml)
4. 4
   Dryingdried over MgSO4
5. 5
   Otherevaporated
6. 6
   Otherto give a crude product, which
7. 7
   Otheris crystallized from ethanol

Procedure

To a mixture of aluminum trichloride (3.0 g, 22.5 mmol), dichloromethane (50 ml) and 2,5-dichloro-2,5-dimethylhexane (15.0 g, 81.9 mmol) is added dropwise into a solution of phenol (7.7 g, 81.90 mmol) in 50 ml of methane dichloride, then the reaction mixture is heated for 4 hours at 35° C. After cooled, the reaction mixture is poured into ice (200 g) and extracted with ether (3×80 ml). The organic phase is washed with 10% NaHCO3 solution (2×150 ml), dried over MgSO4 and evaporated to give a crude product, which is crystallized from ethanol to give the title compound (15.20 g, 84%).

Source