Реакция #10030

Уравнение реакции

N-methylformanilide

butyl vinyl ether

bis-trichloromethylcarbonate

sodium hydroxide

→

pure compound

Выход 69.0%

N-methyl-N-phenylaminoacrolein

Выход 69.0%

Растворители

Water

clorobenzene

clorobenzene

Условия реакции

Обработка

1. 1
   Температураthe mixture is cooled at about 5–10° C.
2. 2
   ДругоеAfter separation of the phases
3. 3
   Экстракцияthe aqueous layer is extracted with chlorobenzene (50 ml)
4. 4
   Промывкаthe combined organic layers are washed with water (20 ml)
5. 5
   Другоеevaporated under reduced pressure
6. 6
   workup.ADDITIONTo the residue tert-butyl methyl ether (50 ml) is added
7. 7
   Температураthe mixture is cooled at −15° C. for 1 hour
8. 8
   ФильтрацияThe precipitate is filtered on Buchner
9. 9
   Промывкаwashed twice with tert-butyl methyl ether (25 ml×2)
10. 10
    Другоеdried at 30–35° C. under vacuum overnight

Методика

To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of clorobenzene under stirring at 10° C., a solution of bis-trichloromethylcarbonate (24.3 g) in 50 ml of clorobenzene is added dropwise in 2 hours. The reaction mixture is kept under stirring at room temperature overnight. Water (50 ml) is 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 (50 ml). After separation of the phases, the aqueous layer is extracted with chlorobenzene (50 ml) and the combined organic layers are washed with water (20 ml) and evaporated under reduced pressure. To the residue tert-butyl methyl ether (50 ml) is added and the mixture is cooled at −15° C. for 1 hour. The precipitate is filtered on Buchner, washed twice with tert-butyl methyl ether (25 ml×2) and dried at 30–35° C. under vacuum overnight. 24.66 g of pure compound are obtained (69% molar yield)

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