反应 #10029

反应方程式

bis-trichloromethylcarbonate

N-methylformanilide

butyl vinyl ether

→

pure compound

收率 70.6%

N-methyl-N-phenylaminoacrolein

收率 70.6%

溶剂

1,4-dioxane

1,4-dioxane

反应条件

后处理

1. 1
   其他the solvent is evaporated under reduced pressure
2. 2
   workup.ADDITIONTert-butyl methyl ether (75 ml) and water (55 ml) are added
3. 3
   温度the mixture is cooled at about 5–10° C.
4. 4
   workup.ADDITIONby adding sodium hydroxide 30% aqueous solution (55 g)
5. 5
   其他After separation of the phases
6. 6
   萃取the aqueous layer is extracted with tert-butyl methyl ether (70 ml)
7. 7
   其他the combined organic layers are evaporated under reduced pressure
8. 8
   workup.ADDITIONTo the residue tert-butyl methyl ether (50 ml) is added
9. 9
   温度the mixture is cooled at −15° C. for 90 minutes
10. 10
    过滤The precipitate is filtered on Buchner
11. 11
    洗涤washed twice with tert-butyl methyl ether (25 ml×2)
12. 12
    其他dried at room temperature under vacuum overnight

实验过程

To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of 1,4-dioxane under stirring at 10–15° C., a solution of bis-trichloromethylcarbonate (28.3 g) in 50 ml of 1,4-dioxane is added dropwise in 90 min. The reaction mixture is kept under stirring at room temperature overnight, then the solvent is evaporated under reduced pressure. Tert-butyl methyl ether (75 ml) and water (55 ml) are added, the mixture is cooled at about 5–10° C. and the pH is corrected to about 7 by adding sodium hydroxide 30% aqueous solution (55 g). After separation of the phases, the aqueous layer is extracted with tert-butyl methyl ether (70 ml) and the combined organic layers are evaporated under reduced pressure. To the residue tert-butyl methyl ether (50 ml) is added and the mixture is cooled at −15° C. for 90 minutes. The precipitate is filtered on Buchner, washed twice with tert-butyl methyl ether (25 ml×2) and dried at room temperature under vacuum overnight. 25.21 g of pure compound are obtained (70% molar yield)

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