Reaktion #95198

Reaktionsgleichung

water

butanedione monoxime

triethylamine

methacryloyl chloride

→

OBM

3-oximino-2-butanone methacrylate

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe monomer 3-oximino-2-butanone methacrylate (OBM) was prepared
2. 2
   Temperaturby cooling to a temperature of 0 degree C
3. 3
   Sonstigewas continued under nitrogen at 0 degree
4. 4
   workup.ADDITIONfor 3 hours after the addition
5. 5
   FiltrationThe resulting mixture was filtered
6. 6
   Sonstigeto remove the solid residues
7. 7
   Sonstigethe liquid obtained
8. 8
   Sonstigewas transferred to a separatory funnel
9. 9
   workup.STIRRINGthe liquid was agitated
10. 10
    SonstigeThe water and ether phases were separated
11. 11
    Trocknenthe ether phase was dried over magnesium sulfate for 1 hour
12. 12
    SonstigeThe magnesium sulfate was removed by filtration
13. 13
    Sonstigethe ether solution was evaporated to dryness on a rotary evaporator
14. 14
    SonstigeThe resulting solid was recrystallized from cyclohexane

Vorschrift

The monomer 3-oximino-2-butanone methacrylate (OBM) was prepared. This preparation began by cooling to a temperature of 0 degree C. with an ice water bath, a solution of butanedione monoxime (54.5 g) and triethylamine (120 ml) in ether (1000 ml). Approximately 56 ml of methacryloyl chloride in 250 ml of ether was added dropwise under a nitrogen atmosphere over the course of 1 hour. The solution was stirred during this addition and the stirring was continued under nitrogen at 0 degree C. for 3 hours after the addition was completed. The resulting mixture was filtered to remove the solid residues. The solid residues were discarded, and the liquid obtained was transferred to a separatory funnel. Approximately 300 ml of water was added to the separatory funnel and the liquid was agitated. The water and ether phases were separated, the water phase was discarded, and the ether phase was dried over magnesium sulfate for 1 hour. The magnesium sulfate was removed by filtration and the ether solution was evaporated to dryness on a rotary evaporator using water aspirator vacuum. The resulting solid was recrystallized from cyclohexane to yield 45 g of OBM. (The material obtained melted between 38.5 and 39 degrees C.)

Quelle