Anisole → 6-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene

HRID 1883263Notes

Reaction equation

HRID 1883263 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

Reactant 3

HCID 7519AnisoleHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 103310036-Methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene

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%).

Workup

  1. additionthe mixture was poured onto ice
  2. extractionextracted with hexane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe excess anisole was removed by vacuum distillation

Sources & evidence

ORD record
ord-0bb82593d2a4451c96de01d9481c4f3f
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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