反应 #501390

反应方程式

2,2-dimethyl-1,3-propanediol

sulfuric acid

3,6-dichloropyridazine

ammonium persulfate

→

3,6-dichloro-4-(1-hydroxymethyl-1-methylethyl)pyridazine

溶剂

water

water

water

反应条件

后处理

1. 1
   workup.ADDITIONTo a 5-liter flask were added 341 g
2. 2
   workup.ADDITIONTo the mixture was then added
3. 3
   workup.ADDITIONThe addition
4. 4
   其他rose from 33° to 86°
5. 5
   workup.ADDITIONWhen the addition
6. 6
   其他the insulating mantle was removed
7. 7
   其他the flask was placed in a water bath
8. 8
   温度to cool it
9. 9
   其他had reached 40°
10. 10
    workup.ADDITIONof dichloromethane was added
11. 11
    过滤filtered through a polypropylene
12. 12
    过滤filter pad
13. 13
    洗涤The solids were washed with 500 ml
14. 14
    其他of dichloromethane, and the layers of the combined filtrate were separated
15. 15
    萃取The aqueous layer was extracted with 1 liter of dichloromethane
16. 16
    萃取the combined organic layers were extracted with 1 liter of water
17. 17
    干燥dried over sodium sulfate
18. 18
    其他The solvent was removed under vacuum
19. 19
    其他to leave 385 g
20. 20
    其他Most of the solid was removed
21. 21
    workup.DISSOLUTIONdissolved in 1200 ml
22. 22
    其他at 85°
23. 23
    温度It was then cooled to 0°
24. 24
    过滤filtered
25. 25
    洗涤the solids were washed with cold toluene
26. 26
    其他dried under vacuum
27. 27
    其他to obtain 152 g

实验过程

To a 5-liter flask were added 341 g. of 2,2-dimethyl-1,3-propanediol, 500 ml. of water, 223 g. of 3,6-dichloropyridazine, 100 ml. of sulfuric acid in 900 ml. of water and 51 g. of silver nitrate. To the mixture was then added, dropwise, with an insulating mantle around the flask, 600 g. of ammonium persulfate dissolved in 1 liter of water. The addition was carried out in about 20 minutes, while the temperature rose from 33° to 86°. When the addition was complete, the insulating mantle was removed and the flask was placed in a water bath to cool it. When the temperature had reached 40°, 1200 ml. of dichloromethane was added and the mixture was stirred for 10 minutes more and filtered through a polypropylene filter pad. The solids were washed with 500 ml. of dichloromethane, and the layers of the combined filtrate were separated. The aqueous layer was extracted with 1 liter of dichloromethane, and the combined organic layers were extracted with 1 liter of water, and dried over sodium sulfate. The solvent was removed under vacuum, to leave 385 g. of a gummy solid. Most of the solid was removed and dissolved in 1200 ml. of toluene at 85°. It was then cooled to 0° and filtered, and the solids were washed with cold toluene and dried under vacuum to obtain 152 g. of the desired intermediate product, 97% pure by nuclear magnetic resonance analysis, m.p. 133°-136°.

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