Anisole → 6-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene
Reaction equation
Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[C:11]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:18][O:17][C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:2]2([CH3:10])[CH3:3]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2,5-dichloro-2,5-dimethyl-hexane (Intermediate 1, 25.3 g, 0.14 mol) in anisole (60 mL, 0.55 mol) at 0° C. was added AlCl3 (18.4 g, 0.14 mmol) portionwise. After stirring for 2 h at 0° C., the mixture was poured onto ice and extracted with hexane. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The excess anisole was removed by vacuum distillation and the title compound was obtained as a white solid upon cooling (30.5 g, 100%).