Hydroxyamine hydrochloride → HCID 86742368, compound

HRID 35281Notes

Reaction equation

HRID 35281 reaction equation
Cl.[NH2:2][OH:3].[O:4]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](=O)[CH3:20])=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.[OH-].[Na+].C(O)C>[O:4]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](=[N:2][OH:3])[CH3:20])=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 212962814-(4-Phenoxyphenyl)-2-butanone

Product 1

HCID 86742368HCID 86742368, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Over about 30 minutes, a freshly prepared solution of 15.3 g (0.22 mole) of hydroxylamine hydrochloride in 100 ml of water and 200 ml of 1N sodium hydroxide solution is added dropwise at room temperature to a solution of 48 g (0.2 mole) of 4-(4-phenoxyphenyl)-2-butanone*) in 500 ml of ethanol. Subsequently, the mixture is heated for 1.5 hours at reflux temperature and then stirred for 16 hours at room temperature. The ethanol is distilled off in a water jet vacuum and the residue is extracted repeatedly with ether. The combined ethereal phases are washed repeatedly with water and dried over sodium sulfate and the ther is distilled off entirely. The crude oxime is chromatographed over silica gel (eluant: a 1:1 mixture of diethyl ether and n-hexane). The resultant 4-(4-phenoxyphenyl)-2-butanone oxime melts at 80°-82° C. after recrystallisation in a mixture of diethyl ether and n-hexane.

Workup

  1. temperatureSubsequently, the mixture is heated for 1.5 hours
  2. temperatureat reflux temperature
  3. distillationThe ethanol is distilled off in a water jet vacuum
  4. extractionthe residue is extracted repeatedly with ether
  5. washThe combined ethereal phases are washed repeatedly with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe ther is distilled off entirely
  8. customThe crude oxime is chromatographed over silica gel (eluant
  9. additiona 1:1 mixture of diethyl ether and n-hexane)
  10. customThe resultant 4-(4-phenoxyphenyl)-2-butanone oxime melts at 80°-82° C. after recrystallisation
  11. additionin a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-6beda3f88e7345d997eba55f398c8c65
Source dataset
uspto-grants-1988_08
Patent number
US04766152

Reaction notes

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