O-Cresol → 3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro2-naphthol

Reaction equation

Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:11][C:12]1[C:13]([OH:18])=[CH:14][C:15]2[C:2]([CH3:10])([CH3:3])[CH2:4][CH2:5][C:6]([CH3:8])([CH3:7])[C:16]=2[CH:17]=1

Participants

Procedure

50.8 g (0.27 mol) of 2,5-dichloro-2,5-dimethylhexane, 30 g (0.27 mol) of 2-methylphenol and 500 ml of dichloromethane were introduced into a three-necked flask. 14.8 g (0.11 mol) of aluminum chloride were added in small amounts at 0° C. and the entire contents were stirred at room temperature for twelve hours. The reaction medium was poured into ice-cold water, extracted with dichloromethane, the organic phase decanted off, washed with sodium bicarbonate, dried over magnesium sulfate and evaporated.