3-Hydroxyacetophenone → 1-(3-Hydroxyphenyl)ethanone oxime

HRID 449518Notes

Reaction equation

HRID 449518 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[OH:9][C:10]1[CH:11]=[C:12]([C:16](=O)[CH3:17])[CH:13]=[CH:14][CH:15]=1>C(O)C.O.C(OCC)(=O)C>[OH:9][C:10]1[CH:11]=[C:12]([C:16](=[N:2][OH:3])[CH3:17])[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 84873-HydroxyacetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 727653751-(3-Hydroxyphenyl)ethanone oximeYield 113.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Hydroxylamine hydrochloride (1 g, 10 mmol) and sodium acetate (1 g, 10 mmol) were added to a solution of 1-(3-hydroxyphenyl)ethanone (Aldrich, Cat. #H18801) (1 g, 7 mmol) in ethanol (30 mL) and water (4 mL). The reaction was heated at 80° C. for 2 h. The reaction was allowed to cool to r.t. and taken up in ethyl acetate and washed with 1 N HCl. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give crude 1-(3-hydroxyphenyl)ethanone oxime (1.2 g, 100%) as yellow oil. Analytical LCMS (M+H)+: m/z=151.9.

Workup

  1. temperatureto cool to r.t.
  2. washwashed with 1 N HCl
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46a8036b8716497b8bc8f04f3353ef33
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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