反应详情

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).

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