Reaktion #80948

Reaktionsgleichung

methyl 2-hydroxy-4-(acetylamino)benzoate

sodium hydride

3-chloro-2-methyl -1-propene

→

methyl 4-(acetylamino)-2-[(2-methyl-2-propenyl)oxy]benzoate

Ausbeute 50.0%

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 3 days at 50° C
3. 3
   SonstigeThe reaction mixture was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane
5. 5
   WaschenThis solution was washed with water, sodium hydroxide 10% and water
6. 6
   Sonstigewas then dried
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue was crystallized from 2,2'-oxybispropane
10. 10
    FiltrationThe product was filtered off
11. 11
    Sonstigedried

Vorschrift

To a solution of 104.6 parts of methyl 2-hydroxy-4-(acetylamino)benzoate in 470 parts of N,N-dimethylformamide were added portionwise 24 parts of a dispersion of sodium hydride in mineral oil (50%) under a nitrogen atmosphere. After stirring for 1 hour at room temperature, there was added a solution of 55.2 parts of 3-chloro-2-methyl -1-propene in 47 parts of N,N-dimethylformamide. Stirring was continued for 3 days at 50° C. The reaction mixture was evaporated and the residue was dissolved in dichloromethane. This solution was washed with water, sodium hydroxide 10% and water and was then dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 65.8 parts (50.0%) of methyl 4-(acetylamino)-2-[(2-methyl-2-propenyl)oxy]benzoate (interm. 15).

Quelle