3,4-Dimethoxyphenyl methyl ketone → Ethanone,1-(3,4-dimethoxyphenyl)-, oxime

HRID 2301933Notes

Reaction equation

HRID 2301933 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:19](=O)[CH3:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]>O.C(O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:19](=[N:2][OH:3])[CH3:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 3

HCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 2779100Ethanone,1-(3,4-dimethoxyphenyl)-, oximeYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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 stirring solution of 3′,4′-dimethoxyacetophenone (5.41 grams, 30.0 mmol) in a mixture of water (30 milliliters) and ethanol (30 milliliters), the solution was stirred overnight. The resulting mixture was filtered and the solid was dried in vacuo (60° C., <1 mm) to afford 4.68 grams (80%) of product as a yellow solid: mp 137-138° C.; 1H NMR (CDCl3) δ7.34-7.08 (m, 2H), 6.94-6 80 (m, 1H), 3.92 (s, 3H ), 3.90 (s, 3H), 2.28 (s , 3H); 13C NMR (CDCl3) δ155.6, 150.1, 148.8, 129.2, 119.2, 110.6, 108.6, 55.8.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe solid was dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-19d0ba4e5e684c54b9455494bbb68f21
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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