反应详情

温度

-15 °C

Into a 2 liter 3-necked round bottom flask equipped with a mechanical stirrer, thermometer, and inlet was charged with agitation 230.394 g (1076.60 mmol) of potassium iodate, 400 g (4341.13 mmol) of toluene and 360 mL of acetic anhydride. The mixture was cooled to -15° C. Trifluoromethanesulfonic acid (325.751 g, 2170.57 mmol) was added dropwise at a rate such that the temperature remained below 5° C. The addition was complete in 2.5 hours. The mixture was allowed to stir for 4 hours at 0° C. The cooling bath was removed and stirring was continued overnight. The mixture was cooled to 0° C. and 537 mL of water was added at such a rate that the temperature remained below 10° C. Dichloromethane (500 mL) was added and the mixture was stirred 30 minutes and allowed to phase split. The dichloromethane phase was separated. To the aqueous phase was added 500 mL of dichloromethane and the mixture was stirred for 30 minutes and allowed to phase split. The dichloromethane phase was separated. The combined dichloromethane phases were concentrated in vacuo at 40° C. to give a brown liquid. Isopropyl ether (800 mL) was added and the mixture was stirred for one hour. The resulting solid was collected by filtration and washed with 800 mL of isopropyl ether. To the solid was added 460 mL of isopropyl alcohol and the mixture was heated to 82° C. for 30 minutes or until the solid dissolved. The solution was diluted with 460 mL of hexane and the mixture was cooled to 0° C. The resulting solid was collected by filtration and washed with a mixture of 200 mL of hexane and 200 mL of isopropyl alcohol. The solid was heated with 460 mL of isopropyl alcohol at 82° C. for 30 minutes or until a homogeneous solution was obtained. The solution was diluted with 460 mL of hexane and the mixture was cooled to 0° C. The solid was collected by filtration and washed with a mixture of 200 mL of hexane and 200 mL of isopropyl alcohol. The solid was then washed with 300 mL of hexane and allowed to air dry to give a white solid (213.92 grams, 43.5% yield, melting point 110-127).

1. customInto a 2 liter 3-necked round bottom flask equipped with a mechanical stirrer
2. customremained below 5° C
3. additionThe addition
4. customThe cooling bath was removed
5. stirringstirring
6. waitwas continued overnight
7. temperatureThe mixture was cooled to 0° C.
8. addition537 mL of water was added at such a rate that the temperature
9. customremained below 10° C
10. additionDichloromethane (500 mL) was added
11. stirringthe mixture was stirred 30 minutes
12. customsplit
13. customThe dichloromethane phase was separated
14. additionTo the aqueous phase was added 500 mL of dichloromethane
15. stirringthe mixture was stirred for 30 minutes
16. customsplit
17. customThe dichloromethane phase was separated
18. concentrationThe combined dichloromethane phases were concentrated in vacuo at 40° C.
19. customto give a brown liquid
20. stirringthe mixture was stirred for one hour
21. filtrationThe resulting solid was collected by filtration
22. washwashed with 800 mL of isopropyl ether
23. additionTo the solid was added 460 mL of isopropyl alcohol
24. temperaturethe mixture was heated to 82° C. for 30 minutes or until the solid
25. dissolutiondissolved
26. additionThe solution was diluted with 460 mL of hexane
27. temperaturethe mixture was cooled to 0° C
28. filtrationThe resulting solid was collected by filtration
29. washwashed with a mixture of 200 mL of hexane and 200 mL of isopropyl alcohol
30. temperatureThe solid was heated with 460 mL of isopropyl alcohol at 82° C. for 30 minutes or until a homogeneous solution
31. customwas obtained
32. temperaturethe mixture was cooled to 0° C
33. filtrationThe solid was collected by filtration
34. washwashed with a mixture of 200 mL of hexane and 200 mL of isopropyl alcohol
35. washThe solid was then washed with 300 mL of hexane
36. customto air dry
37. customto give a white solid (213.92 grams, 43.5% yield, melting point 110-127)