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

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dichloro-2,5-dimethyl-hexane (Intermediate 1, 97 g, 0.53 mol) and phenol (50 g, 0.53 mol) in CHCl3 (500 mL) at 0° C. was added AlCl3 (71 g, 0.54 mmol) portionwise. After stirring for 2 h at 0° C., the mixture was poured onto ice and was extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. Recrystallization of the resulting solid from Et2O-hexane (1:1) gave the title compound as off-white crystals (95.7 g, 89%).

Provenance & Evidence