Water → Cyclohexanone, 2-(3-methoxyphenyl)-, oxime

HRID 1594919Notes

Reaction equation

HRID 1594919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=O)[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+].O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[N:17][OH:18])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 858682-(3-Methoxyphenyl)cyclohexanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 2728109Cyclohexanone, 2-(3-methoxyphenyl)-, oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-Methoxyphenyl)-cyclohexanone, as described in Step A above, (0.61 g, 3 mmol), hydroxylamine hydrochloride (0.40 g, 6 mmol) and sodium acetate (0.80, 6.2 mmol) were combined in EtOH (4 mL): H2O (2 mL) and heated at reflux for 3 h. The reaction mixture was concentrated, then partitioned between EtOAc (100 mL) and H2O (100 mL), the organic layer separated, washed with H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc (100 mL) and H2O (100 mL)
  4. customthe organic layer separated
  5. washwashed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-0723351be00e4feaab4906a065b4772b
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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