反应详情

To a solution of 4-aminophenol (5.00 g, 45.8 mmol) in dichloromethane (50 ml) were added cyclohexanecarbonyl chloride (6.72 g, 45.8 mmol) and pyridine (3.70 ml, 45.8 mmol), while cooling the reaction mixture in an ice bath. After the addition was completed, the cooling bath was removed and stirring was continued overnight at room temperature. Water (100 ml) was added, the dichloromethane was removed by evaporation and the resulting solution was extracted with ethyl acetate (3×300 ml). The combined organic phases were washed with water (2×200 ml), dried, filtered and evaporated, yielding an off-white solid. The crude product was purified by flash column chromatography (SiO2, ethyl acetate/heptane (2:3)), yielding a mixture of two compounds, which were dissolved in THF. 6N NaOH (aq, 32 ml) was added and the mixture was stirred at room temperature for 2.5 h. The solution was acidified with concentrated hydrochloric acid. The THF was removed by evaporation. The solid material was collected by filtration, dried in vacuo and recrystallised (ethyl acetate/heptane), yielding the title compound (4.20 g, 41%, off-white solid).

1. temperaturewhile cooling the reaction mixture in an ice bath
2. additionAfter the addition
3. customthe cooling bath was removed
4. additionWater (100 ml) was added
5. customthe dichloromethane was removed by evaporation
6. extractionthe resulting solution was extracted with ethyl acetate (3×300 ml)
7. washThe combined organic phases were washed with water (2×200 ml)
8. customdried
9. filtrationfiltered
10. customevaporated
11. customyielding an off-white solid
12. customThe crude product was purified by flash column chromatography (SiO2, ethyl acetate/heptane (2:3))
13. customyielding
14. additiona mixture of two compounds, which
15. stirringthe mixture was stirred at room temperature for 2.5 h
16. customThe THF was removed by evaporation
17. filtrationThe solid material was collected by filtration
18. customdried in vacuo
19. customrecrystallised (ethyl acetate/heptane)