反应详情

1-Cyclohex-1-enyl-4-nitrobenzene (11.7 g, 57.6 mmol) was dissolved in hot absolute ethanol (170 mL). Stannous chloride (65 g, 288 mmol) was added and the reaction mixture was stirred at reflux temperature for 1.5 hours. The reaction mixture was concentrated in vacuo and the residue was added ethyl acetate (700 mL) and water (700 mL), and neutralised to pH 7 with sodium hydroxide (4 N). Ethyl acetate (150 mL) was added and the mixture was filtered through celite. The organic phase of the filtrate was washed with water and a saturated solution of sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was purified on silica (200 g) using ethyl acetate and heptane (1:4) as eluent to give 7.4 g of 4-(cyclohex-1-enyl)phenylamine.

1. temperatureat reflux temperature for 1.5 hours
2. concentrationThe reaction mixture was concentrated in vacuo
3. additionthe residue was added ethyl acetate (700 mL) and water (700 mL)
4. additionEthyl acetate (150 mL) was added
5. filtrationthe mixture was filtered through celite
6. washThe organic phase of the filtrate was washed with water
7. dry with materiala saturated solution of sodium chloride, dried over MgSO4
8. concentrationconcentrated in vacuo
9. customThe residue was purified on silica (200 g)