Water → 3-Hydroxyiminobutan-2-one;2-methylprop-2-enoic acid

HRID 66920Notes

Reaction equation

HRID 66920 reaction equation
[CH3:1][C:2](=[N:6][OH:7])[C:3](=[O:5])[CH3:4].C(N(CC)CC)C.[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17].O>CCOCC>[C:15]([OH:19])(=[O:5])[C:16]([CH3:18])=[CH2:17].[N:6](=[C:2]([CH3:1])[C:3](=[O:5])[CH3:4])[OH:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 63989692-Oxime 2,3-butanedione

Product 1

HCID 738798013-Hydroxyiminobutan-2-one;2-methylprop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.)

Workup

  1. customThe monomer 3-oximino-2-butanone methacrylate (OBM) was prepared
  2. temperatureby cooling to a temperature of 0 degree C
  3. customwas continued under nitrogen at 0 degree
  4. additionfor 3 hours after the addition
  5. filtrationThe resulting mixture was filtered
  6. customto remove the solid residues
  7. customthe liquid obtained
  8. customwas transferred to a separatory funnel
  9. stirringthe liquid was agitated
  10. customThe water and ether phases were separated
  11. dry with materialthe ether phase was dried over magnesium sulfate for 1 hour
  12. customThe magnesium sulfate was removed by filtration
  13. customthe ether solution was evaporated to dryness on a rotary evaporator
  14. customThe resulting solid was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-5ff3b8f09cfb48e092f5800cf9912f1a
Source dataset
uspto-grants-1982_08
Patent number
US04343889

Reaction notes

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