Ethanol → 3-Phenoxybutan-2-one oxime

HRID 1288235Notes

Reaction equation

HRID 1288235 reaction equation
[O:1]([CH:8]([CH3:12])[C:9](=O)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl.[NH2:17][OH:18]>O>[O:1]([CH:8]([CH3:12])[C:9](=[N:17][OH:18])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 27644743-Phenoxy-2-butanone

Product 1

HCID 867340893-Phenoxybutan-2-one oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Phenoxybutan-2-one (69.6 g.) and ethanol (300 ml.) were added to a solution of hydroxylamine hydrochloride (70 g.) and fused sodium acetate (70 g.) in water (130 ml.). The resulting solution was refluxed for 31/2 hours and evaporated to near dryness under reduced pressure. The residue was partitioned between water and ether. The ether extract was washed with water, dried over anhydrous potassium carbonate and evaporated. The residue was distilled to give a fraction, b.p. 154°-155°/14 mm. which crystallised. Recrystallisation from petroleum ether (b.p. 60°-80°) gave pure 3-phenoxybutan-2-one oxime, m.p. 65°-67°.

Workup

  1. temperatureThe resulting solution was refluxed for 31/2 hours
  2. customevaporated
  3. customThe residue was partitioned between water and ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous potassium carbonate
  7. customevaporated
  8. distillationThe residue was distilled
  9. customto give a fraction, b.p. 154°-155°/14 mm
  10. customwhich crystallised
  11. customRecrystallisation from petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-109a364803a944dbae0328df6d223e6f
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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