反应详情

Phenylmagnesium bromide-ether solution was prepared from bromobenzene (64.5g, 0.41m), magnesium turnings (9.85g, 0.41m), and anhydrous ether (500ml). The reagent was cooled and (+)-β-methylbutyl-4-toluenesulfonate (200g, 0.82m) in ether (800ml) was added in drops. When the addition was complete, the reaction mixture was stirred for two hours, refluxed for two hours and left to stand overnight. Aqueous sulfuric acid was added until a clear solution was formed. The layers were separated. The aqueous layer was extracted with ether (3×250ml), and the combined organic layers were washed with sodium bicarbonate solution, water and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was steam-distilled. Fractional distillation of the crude product at reduced pressure yielded (+)-β-methylbutylbenzene (38.7g, 64.8%), bp. 74°-77° C at 12 mm pressure.

1. temperatureThe reagent was cooled
2. additionWhen the addition
3. temperaturerefluxed for two hours
4. waitleft
5. waitto stand overnight
6. customwas formed
7. customThe layers were separated
8. extractionThe aqueous layer was extracted with ether (3×250ml)
9. washthe combined organic layers were washed with sodium bicarbonate solution, water
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was evaporated
12. distillationthe residue was steam-distilled
13. distillationFractional distillation of the crude product at reduced pressure