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

HRID 2388172Notes

Reaction equation

HRID 2388172 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].CO.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH2:19][CH3:20])=[CH:14][CH:13]=1>O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[N:2][OH:3])[CH2:19][CH3:20])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 680044-FluoropropiophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 737932191-(4-Fluorophenyl)propan-1-one oximeYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (7.5 g, 108 mmol) and sodium acetate (8.9 g, 108 mmol) were added to 50 mL of methanol and the resulting white slurry was stirred at room temperature for 30 min. 1-(4-Fluorophenyl)propan-1-one (15 g, 98.6 mmol) was added and the mixture was stirred at room temperature 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 16.4 g of the title compound. MS: (+) m/z 168.36 (M+1).

Workup

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

Sources & evidence

ORD record
ord-a68a0b1cc15249129def1b4ec7b00ce2
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…