Hydroxylamine HCl → 5-methylhex-5-en-2,3-dione 3-(O-methyloxime) 2-oxime

HRID 2228845Notes

Reaction equation

HRID 2228845 reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:5](=O)[CH3:6].[Cl-].[OH:13][NH3+:14]>CO.O.N1C=CC=CC=1>[CH3:1][O:2][N:3]=[C:4]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:5](=[N:14][OH:13])[CH3:6]

Participants

6

Reactant 2

HCID 21645Hydroxylamine HClHCID 54346298HCID 54346298, compound

Product 1

HCID 1363835465-methylhex-5-en-2,3-dione 3-(O-methyloxime) 2-oxime

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
23 °C

Procedure

283.4 g of 5-methylhex-5-ene-2,3-dione 3-(O-methyloxime) in 800 ml of methanol were added dropwise to the solution of 140.6 g of hydroxylammonium chloride in 400 ml of water and 216.7 g of pyridine, and the mixture was stirred at 23° C. for 3 hours. The solvent was then removed under reduced pressure and the residue was poured into ice-water. The pH was subsequently adjusted to 1 using 20% strength sulfuric acid, and the precipitated product was filtered off with suction, taken up in methyl tert-butyl ether and washed with water. The organic phase was then dried over sodium sulfate and the solvent was removed under reduced pressure. This gave 266 g of the title compound as a colorless solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionthe residue was poured into ice-water
  3. filtrationthe precipitated product was filtered off with suction
  4. washwashed with water
  5. dry with materialThe organic phase was then dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-adaeb010e171493b90c79b95123bf649
Source dataset
uspto-grants-2002_07
Patent number
US06417388B1

Reaction notes

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