4-Nitrophenol → 1-(4-Nitrophenoxy)propan-2-one

HRID 865403Notes

Reaction equation

HRID 865403 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19](=[O:21])[CH3:20]>CC(C)=O>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][CH2:18][C:19](=[O:21])[CH3:20])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 6571ChloroacetoneHCID 11430Potassium Carbonate

Product 1

HCID 3085071-(4-Nitrophenoxy)propan-2-oneYield 82.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into acetone (300 ml ) were suspended 41.7 g (0.3 mol) of p-nitrophenol and 41.4 g (0.3 mol) of anhydrous potassium carbonate. Under stirring and reflux, 27.7 g (0.3 mol) of chloroacetone were added dropwise therein over five hours. After the resulting mixture was reacted for two hours as it was, it was cooled down, and the reaction liquid was dispersed into ice water (500 ml). After the extract obtained by extraction therefrom with ethyl acetate (500 ml) was washed with water and dried, the solvent was distilled off under reduced pressure. The thus-obtained light-yellow crystalline residue was recrystallized from ethyl acetate/n-hexane, whereby 48.1 g of the title compound were obtained. (Yield: 82.2%)

Workup

  1. temperaturereflux
  2. customAfter the resulting mixture was reacted for two hours as it
  3. temperatureit was cooled down
  4. customthe reaction liquid
  5. customAfter the extract obtained by extraction
  6. washwith ethyl acetate (500 ml) was washed with water
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe thus-obtained light-yellow crystalline residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e1f2330249f94067906361563d1fbdbe
Source dataset
uspto-grants-1996_10
Patent number
US05565586

Reaction notes

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