Water → HCID 73668580, compound

HRID 274916Notes

Reaction equation

HRID 274916 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:4]=1[CH:5]=O.[OH2:18].Cl.[NH2:20]O.C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:4]=1[CH:5]=[N:20][OH:18]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 199760832-Methoxy-5-phenoxybenzaldehyde

Product 1

HCID 73668580HCID 73668580, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methoxy-5-phenoxybenzaldehyde (4.5 g, 19.7 mmol) was dissolved in 60 ml of warm methanol. Water (40 ml) was added to this solution followed by the addition of hydroxylamine hydrochloride (2.7 g, 38.9 mmol) and anhydrous sodium acetate (6.5 g, 79.2 mmol). This mixture was then refluxed for 4 hours. The reaction mixture was concentrated under reduced pressure to remove the methanol. The residue was partitioned with ethyl acetate. The ethyl acetate layer was separated, washed five times with water, dried (anhydrous MgSO4) and the solvent removed under reduced pressure to give 2-methoxy-5-phenoxybenzaldehyde oxime as a white crystalline solid (4.70 g, 98%), mp 95°-100° C.

Workup

  1. temperatureThis mixture was then refluxed for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove the methanol
  4. customThe residue was partitioned with ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed five times with water
  7. dry with materialdried (anhydrous MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2075e5cf2887400e9b0aabec6c8f472b
Source dataset
uspto-grants-1995_02
Patent number
US05391571

Reaction notes

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