Sodium Hydroxide → 1-Phenyl-2-(3-methoxyphenyl)ethanone oxime

HRID 2231205Notes

Reaction equation

HRID 2231205 reaction equation
Cl.[NH2:2][OH:3].[C:4]1([C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[C:4]1([C:10](=[N:2][OH:3])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27596142-(3-Methoxyphenyl)-1-phenylethan-1-one

Product 1

HCID 727291561-Phenyl-2-(3-methoxyphenyl)ethanone oximeYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydroxylamine hydrochloride (185.5 g, 2.67 mol) water (0.3 L) was added with stirring to a solution of 1-phenyl-2-(3-methoxyphenyl)ethanone (187 g, 0.89 mol) in 95% ethanol (1.4 L). Then, 0.3 L of 20% NaOH was added, with stirring, to the resulting mixture. The mixture was heated to reflux for 2 hrs, cooled, and the alcohol was evaporated with a water aspirator. The aqueous residue was extracted with ether (3×500 ml). The combined ether extracts were dried over MgSO4 and evaporated to provide a solid residue which was then recrystallized from cyclohexane (1 L) to provide 165.5 g (82%) of 1-phenyl-2-(3-methoxyphenyl)ethanone oxime. An analytical sample, recrystallized from ethylacetate/cyclohexane, had mp. 72°-73° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hrs
  3. temperaturecooled
  4. customthe alcohol was evaporated with a water aspirator
  5. extractionThe aqueous residue was extracted with ether (3×500 ml)
  6. dry with materialThe combined ether extracts were dried over MgSO4
  7. customevaporated
  8. customto provide a solid residue which
  9. customwas then recrystallized from cyclohexane (1 L)

Sources & evidence

ORD record
ord-7ed2284c13934c2e9e5aa9011bb08bc0
Source dataset
uspto-grants-1988_11
Patent number
US04782058

Reaction notes

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