Réaction #10033

Équation de réaction

N-methylformanilide

butyl vinyl ether

bis-trichloromethylcarbonate

sodium hydroxide

→

N-methyl-N-phenylaminoacrolein

Solvants

clorobenzene

clorobenzene

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is cooled at about 5° C.
2. 2
   AutreAfter separation of the phases
3. 3
   Extractionthe aqueous layer is extracted with chlorobenzene (90 ml)
4. 4
   Lavagethe combined organic layers are washed with water (100 ml)
5. 5
   Autreevaporated under reduced pressure
6. 6
   workup.ADDITIONThe obtained residue (116.9 g, containing, according to HPLC assay, 104.8 g of pure product, 88% molar yield)
7. 7
   Autreis used for the next step of the synthesis without any further purification

Mode opératoire

To a solution of N-methylformanilide (100 g), butyl vinyl ether (74.12 g) in 85 ml of clorobenzene under stirring at 5° C., a solution of bis-trichloromethylcarbonate (87.84 g) in 170 ml of clorobenzene is added dropwise in 2 hours. The reaction mixture is kept under stirring at room temperature overnight. The mixture is cooled at about 5° C. and the pH is corrected to about 7 by adding sodium hydroxide 15% aqueous solution (348 ml). After separation of the phases, the aqueous layer is extracted with chlorobenzene (90 ml) and the combined organic layers are washed with water (100 ml) and evaporated under reduced pressure. The obtained residue (116.9 g, containing, according to HPLC assay, 104.8 g of pure product, 88% molar yield) is used for the next step of the synthesis without any further purification.

Source