Methanol → 1-(4-Methoxyphenyl)propan-1-one oxime

HRID 2388179Notes

Reaction equation

HRID 2388179 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].CO.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[CH2:20][CH3:21])=[CH:15][CH:14]=1>O>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[N:2][OH:3])[CH2:20][CH3:21])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 671444-PropanoylanisoleHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 534338901-(4-Methoxyphenyl)propan-1-one oximeYield 111.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (7.0 g, 100 mmol) and sodium acetate (8.2 g, 100 mmol) were added to 50 mL of methanol and the resulting white slurry was stirred at room temperature for 30 min. 1-(4-Methoxyphenyl)propan-1-one (15 g, 91.4 mmol) was added and the mixture was stirred at room temperature for 20 hours, and then refluxed for 20 hours. Water (50 mL) was added and the mixture was stirred for 10 min. The product was extracted with EtOAc and the organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. The solvent was evaporated in vacuo to give 18.3 g of the title compound. MS: (+) m/z 180.39 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. temperaturerefluxed for 20 hours
  3. stirringthe mixture was stirred for 10 min
  4. extractionThe product was extracted with EtOAc
  5. washthe organic layer was washed with saturated NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7da20aac6da648c181b45a31999b8da4
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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