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

HRID 370458Notes

Reaction equation

HRID 370458 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13](=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13](=[O:15])[CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 6571ChloroacetoneHCID 11430Potassium Carbonate

Product 1

HCID 3085071-(4-Nitrophenoxy)propan-2-oneYield 88.6%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture consisting of 35 g of 4-nitrophenol, 35 g of chloroacetone, 35 g of potassium carbonate, 1 g of potassium iodide and 500 ml of acetone was heated at reflux with stirring for 3 hr. Reaction mixture was concentrated underd reduced pressure; the concentrate was extracted with ethyl acetate; the ethyl acetate layer was washed consecutively with 5% aqueous solution of sodium hydroxide, water and saturated saline; and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; the residue was dissolved in 300 ml of ethanol, added with 100 ml of n-hexane; and subsequently left standing overnight at room temperature. Yellow crystals thus isolated were filtered off, dried and yielded 43.5 g of 4-nitrophenoxyacetone.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customReaction mixture
  4. concentrationwas concentrated underd reduced pressure
  5. extractionthe concentrate was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed consecutively with 5% aqueous solution of sodium hydroxide, water and saturated saline
  7. dry with materialand dried with anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. dissolutionthe residue was dissolved in 300 ml of ethanol
  10. additionadded with 100 ml of n-hexane
  11. waitand subsequently left
  12. waitstanding overnight at room temperature
  13. customYellow crystals thus isolated
  14. filtrationwere filtered off
  15. customdried

Sources & evidence

ORD record
ord-d78bc5fb6d944318868a006df69293e8
Source dataset
uspto-grants-1985_07
Patent number
US04526893

Reaction notes

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