Nitric Acid → 1-(4-Methyl-3-nitrophenyl)propan-1-one

HRID 539770

Reaction equation

HRID 539770 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>>[CH3:11][C:1]1[CH:2]=[CH:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][C:6]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 21429p-Methylpropiophenone

Product 1

HCID 232442491-(4-Methyl-3-nitrophenyl)propan-1-oneYield 63%

Conditions

Temperature
0 °C

Procedure

A solution of fuming nitric acid (100 mL) at 0° C. is added dropwise 1-p-tolylpropan-1-one (Sigma-Aldrich, 121 mmol) while maintaining the reaction temperature below 10° C. The reaction mixture is stirred at 0° C. for 1 hour then poured into excess ice water. The mixture is placed in a freezer overnight and precipitate collected by filtration, washed with ice water, and taken up in CH2Cl2. The organic solution is washed with sat. aqueous NaHCO3 (100 mL), organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude is purified via chromatography (hexanes to EtOAc) to afford the title compound (14.8 g, 63%) as a light yellow solid: Rf 0.5 (1:4 EtOAc:hexanes).

Workup

  1. temperaturewhile maintaining the reaction temperature below 10° C
  2. waitThe mixture is placed in a freezer overnight
  3. filtrationprecipitate collected by filtration
  4. washwashed with ice water
  5. washThe organic solution is washed with sat. aqueous NaHCO3 (100 mL), organic layer
  6. customis collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe crude is purified via chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-1f611d5182ff4cb38469e2337f3a165c
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Linked notes

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