Water → 1-(2-Nitrophenyl)propan-2-one

HRID 1576109Notes

Reaction equation

HRID 1576109 reaction equation
[C:1]([C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])=CN(C)C)(=[O:3])[CH3:2].O>O1CCOCC1>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:4][C:1](=[O:3])[CH3:2])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 962WaterHCID 541295954-(Dimethylamino)-3-(2-nitrophenyl)but-3-en-2-one2×

Product 1

HCID 125079331-(2-Nitrophenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product of Example 8, i.e., α-acetyl-β-dimethylamino-2-nitrostyrene was refluxed with a mixture of 8 ml. of water and 25 ml. of dioxane for 24 hours. After cooling, the mixture was concentrated in vacuo and the residue partitioned between methylene chloride and water. The organic phase was washed with brine, dried and concentrated. The crude product was chromatographed on silica gel using benzene, followed by methylene chloride as the eluent to give 926 mg. (26 percent based on β-dimethylamino-2-nitrostyrene) of 1-o-nitrophenyl-2-propanone as an oil. A small amount was recrystallized from hexane to give pale yellow plates of 1-o-nitrophenyl-2-propanone, having a melting point of 24°-25°. The nmr spectrum was in agreement with the proposed structure.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue partitioned between methylene chloride and water
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel
  8. customto give 926 mg
  9. customA small amount was recrystallized from hexane

Sources & evidence

ORD record
ord-26eb2fe15a2b4358883edd43cb548ca9
Source dataset
uspto-grants-1976_09
Patent number
US03979410

Reaction notes

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