Ethanol → Ethanone, 1-(4-hydroxyphenyl)-, oxime

HRID 1200145Notes

Reaction equation

HRID 1200145 reaction equation
C([O-])(=O)C.[Na+].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][CH:8]=1.C(O)C.Cl.[NH2:20][OH:21]>O>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:20][OH:21])[CH3:14])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 74694'-HydroxyacetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 96522Ethanone, 1-(4-hydroxyphenyl)-, oximeYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

115.2 g (1.405 moles) of sodium acetate, 108.9 g (0.800 mole) of p-hydroxyacetophenone and 1000 ml of ethanol were added to a solution of 56.8 g (0.817 mole) of hydroxylamine hydrochloride in 1000 ml of water, and then the mixture was refluxed for 4 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to a volume of about 500 ml, and the concentrate was allowed to cool at room temperature for 23 hours to precipitate crystals. The crystals were washed with 500 ml of water, and dried in air for 24 hours and in vacuo for a further 6 hours to give 102.1 g (84.5%) of p-hydroxyacetophenone oxime in the form of colorless needles melting at 145°-146°.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to a volume of about 500 ml
  3. customto precipitate crystals
  4. washThe crystals were washed with 500 ml of water
  5. customdried in air for 24 hours and in vacuo for a further 6 hours

Sources & evidence

ORD record
ord-2f8dba58949a45358b9bf438054e4b92
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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