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

HRID 2301936Notes

Reaction equation

HRID 2301936 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH3:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=O>O.C(O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11](=[N:2][OH:3])[CH2:10][CH3:9])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 671444-PropanoylanisoleHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 534338901-(4-Methoxyphenyl)propan-1-one oximeYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of hydroxylamine hydrochloride (3.33 grams, 48 mmol) and sodium acetate (4.92 grams, 60 mmol) in 20 milliliters of water was added to a stirred solution of 4-methoxypropiophenone (5.26 grams, 30.0 mmol) in a mixture of water (30 milliliters) and ethanol (30 milliliters), a further 20 milliliters of ethanol was added to get a homogenous solution, which was stirred overnight. The resulting slurry was filtered, the filtrate was partially concentrated, to remove the ethanol and a white solid precipitated. The slurry was filtered and the solid was washed with water, and dried in vacuo (25° C., <1 mm) to afford 5.26 grams (98%) of product as a white solid: 1H NMR (CDCl3) δ7.64-7.42 (m , 2H), 7.04-6.81(m, 2H), 3.82(s, 3H), 2.81(q , J=7.6 Hz), 2H), 1.17(t , J=7.6 Hz, 3H).

Workup

  1. customto get a homogenous solution, which
  2. filtrationThe resulting slurry was filtered
  3. concentrationthe filtrate was partially concentrated
  4. customto remove the ethanol
  5. customa white solid precipitated
  6. filtrationThe slurry was filtered
  7. washthe solid was washed with water
  8. customdried in vacuo (25° C., <1 mm)

Sources & evidence

ORD record
ord-2c99bcabd4464cd6848752608737b742
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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