Reaction #6602

Reaction equation

aluminum chloride

phenol

2,5-dichloro-2,5-dimethylhexane

→

title compound

Yield 32.1%

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

Yield 32.1%

Solvents

Conditions

Workup

1. 1
   Extractionextracted with ether
2. 2
   Washthe organic phase was washed
3. 3
   Dryingdried over sodium sulfate
4. 4
   Otherevaporated under reduced pressure
5. 5
   OtherTwo recrystallizations of the residue from methanol

Procedure

27.5 g (0.2 mol) of anhydrous aluminum chloride were added by spatula to 250.0 g (2.65 mol) of phenol plus 414.5 g (2.27 mol) of 2,5-dichloro-2,5-dimethylhexane in 500 ml of petroleum ether at room temperature while stirring. After 48 hours, the reaction mixture was poured into ice-water and extracted with ether, and the organic phase was washed to neutrality with water, dried over sodium sulfate and evaporated under reduced pressure. Two recrystallizations of the residue from methanol yielded 148.7 g of the title compound of melting point 219°-220 C.

Source