Hydroxylamine → 4-Phenylcyclohexanone oxime

HRID 990691Notes

Reaction equation

HRID 990691 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:14][OH:15]>C(O)C.C(O)(=O)C.ClCCl>[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[N:14][OH:15])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 787HydroxylamineHCID 786054-Phenylcyclohexanone

Product 1

HCID 3438824-Phenylcyclohexanone oxime

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-phenylcyclohexanone (5 g) in ethanol (100 ml) and acetic acid (16.4 ml) was added aqueous hydroxylamine (50%, 4.5 ml). The reaction was heated at reflux for 16 h, before being allowed to cool, and diluted with dichloromethane (100 ml). The reaction was washed with aqueous sodium bicarbonate (sat, 2×50 ml), the organic layer dried over magnesium sulphate (2 g) and the solvent removed in vacuo to yield a white solid. This was purified by flash chromatography (silica, eluent 50% ethyl acetate/hexane), to yield the title compound as a white solid (5.1 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 h
  3. temperatureto cool
  4. washThe reaction was washed with aqueous sodium bicarbonate (sat, 2×50 ml)
  5. dry with materialthe organic layer dried over magnesium sulphate (2 g)
  6. customthe solvent removed in vacuo
  7. customto yield a white solid
  8. customThis was purified by flash chromatography (silica, eluent 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-82e65319d1e4443abab9fb66387df59a
Source dataset
uspto-grants-2002_10
Patent number
US06462042B1

Reaction notes

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