Reacción #10030

Ecuación de reacción

N-methylformanilide

butyl vinyl ether

bis-trichloromethylcarbonate

sodium hydroxide

→

pure compound

Rendimiento 69.0%

N-methyl-N-phenylaminoacrolein

Rendimiento 69.0%

Disolventes

Water

clorobenzene

clorobenzene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)

Fuente