Phenol → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

Aluminum trichloride (25 g, 0.18 mol) was added portions to a solution of phenol (49.5 g, 0.52 mol) and 2,5-dichloro-2,5-dimethylhexane (101.0 g, 0.55 mol) in dichloromethane (700 mL). The reaction mixture was allowed to stir at 25-40° C. for 2 h, then the dark red mixture was poured onto ice water. Aqueous work up (EtOAc extraction) gave 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-ol 84.8 g (80%) as a white solid, which was recrystallized from hexane to give the product as colorless needles: 1H NMR (400 MHz, CDCl3) δ 7.17 (d, 1H, ArH), 6.78 (d, 1H, ArH), 6.62 (dd, 1H, ArH), 4.55 (s, 1H, OH), 1.65 (s, 4H, 2CH2), 1.25 (s, 12H, 4CH3).

Provenance & Evidence