Hydroxyamine hydrochloride → 4-Phenoxyphenoxyacetone oxime

HRID 35279Notes

Reaction equation

HRID 35279 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[O:9]([C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](=O)[CH3:23])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O.C(O)C>[O:9]([C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](=[N:2][OH:3])[CH3:23])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 137717024-Phenoxyphenoxyacetone

Product 1

HCID 867423654-Phenoxyphenoxyacetone oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Over about 1 hour, a solution of 22 g of hydroxylamine hydrochloride and 26 g of anhydrous sodium acetate in 110 ml of water is added dropwise at room temperature to a solution of 64 g of 4-phenoxyphenoxyacetone in 260 ml of ethanol. After the slightly exothermic reaction has subsided, the mixture is stirred for a further 3.5 hours at reflux temperature. Subsequently, the ethanol is distilled off from the reaction mixture by rotary evaporation, the aqueous residue is extracted three times with a 2:1 mixture of ether and hexane, the combined organic phases are washed with water and with 10% sodium bicarbonate solution and then dried over sodium sulfate. The solvent is then distilled off. Recrystallisation from a mixture of diethyl ether and pentane affords 4-phenoxyphenoxyacetone oxime with a melting point of 59°-61° C.

Workup

  1. customAfter the slightly exothermic reaction
  2. temperatureat reflux temperature
  3. distillationSubsequently, the ethanol is distilled off from the reaction mixture by rotary evaporation
  4. extractionthe aqueous residue is extracted three times
  5. additionwith a 2:1 mixture of ether and hexane
  6. washthe combined organic phases are washed with water and with 10% sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent is then distilled off
  9. customRecrystallisation
  10. additionfrom a mixture of diethyl ether and pentane

Sources & evidence

ORD record
ord-f4cb6a7e299043e7b3155f8a624b2916
Source dataset
uspto-grants-1988_08
Patent number
US04766152

Reaction notes

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