Indane → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydrobenz(f)indane

HRID 1017160Notes

Reaction equation

HRID 1017160 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:11]([CH3:19])([CH2:13][CH2:14][C:15](Cl)([CH3:17])[CH3:16])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:12][C:11]1([CH3:19])[C:7]2[C:6](=[CH:5][C:4]3[CH2:3][CH2:2][CH2:1][C:9]=3[CH:8]=2)[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 10326IndaneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 184028515,5,8,8-Tetramethyl-5,6,7,8-tetrahydrobenz(f)indaneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flame dried 3 L three neck round bottom flask fit with a magnetic stirrer, condenser, heating mantle, and nitrogen inlet was charged with indane (49 mL, 0.40 mol, Aldrich), anhydrous methylene chloride (800 mL, Aldrich), and 2,5-dichloro-2,5-dimethylhexane. The mixture was heated to reflux and the aluminum chloride (5.65 g, 0.042 mol). was added portionwise while refluxing the reaction. The reaction mixture was quenched in 1 L 5% HCl/ice, the layers separated, and the combined organics washed with water until neutral to pH paper. The organics were then dried over anhydrous magnesium sulfate, stripped of solvent by rotary evaporation and distilled to yield 5,5,8,8-tetramethyl-5,6,7,8-tetrahydrobenz(f)indane (32.1 g, 105-110° C./0.4-0.45 mm Hg, 76-89% pure by GC). 1HNMR (CDCl3, 500 MHz) δ7.19 (s, 2H); 2.86 (t, J=7.5 Hz, 4H); 2.04 (p, J=7.5 Hz, 2H); 1.67 (s, 4H); 1.28 (s, 12H).

Workup

  1. dry with materialA flame dried 3 L three neck round bottom flask fit with a magnetic stirrer, condenser
  2. temperatureheating mantle
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. additionwas added portionwise
  6. temperaturewhile refluxing
  7. customthe reaction
  8. customThe reaction mixture was quenched in 1 L 5% HCl/ice
  9. customthe layers separated
  10. washthe combined organics washed with water until neutral
  11. dry with materialThe organics were then dried over anhydrous magnesium sulfate
  12. customstripped of solvent by rotary evaporation
  13. distillationdistilled

Sources & evidence

ORD record
ord-f65a4be81a704198a032a61fe7d88dd7
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

Loading…