1-(4-Methoxy-2,5-dimethylphenyl)ethanone → (NE)-N-[1-(4-methoxy-2,5-dimethylphenyl)ethylidene]hydroxylamine

HRID 1619164Notes

Reaction equation

HRID 1619164 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10](=O)[CH3:11])=[C:5]([CH3:13])[CH:4]=1.[Cl-].[NH2:15][OH:16]>CO>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6](/[C:10](=[N:15]/[OH:16])/[CH3:11])=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 149071491-(4-Methoxy-2,5-dimethylphenyl)ethanoneHCID 21878317Hydroxyamine chloride

Product 1

HCID 88531605(NE)-N-[1-(4-methoxy-2,5-dimethylphenyl)ethylidene]hydroxylamineYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.5 g (2.6 mmol) of 1-(4-methoxy-2,5-dimethylphenyl)ethanone obtained in Step 2 and 0.36 g (5.1 mmol) of hydroxylamine chloride in 15 mL of methanol was added 1.0 g of a molecular sieve for dehydration. The reaction mixture was stirred at room temperature for 3 hours and filtered through celite and the filtrate was concentrated in a vacuum. The concentrate was stirred in water (20 mL) and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified through silica gel chromatography to produce (E)-1-(4-methoxy-2,5-dimethylphenyl)ethanone oxime as a white solid (0.45 g, yield: 83%).

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated in a vacuum
  3. stirringThe concentrate was stirred in water (20 mL)
  4. extractionthe aqueous layer was extracted twice with 20 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue was purified through silica gel chromatography

Sources & evidence

ORD record
ord-c3749936d28141e69e3cc21d73007216
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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