4'-Hydroxyacetophenone → HCID 10061000, compound

HRID 1732484Notes

Reaction equation

HRID 1732484 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Br:11][CH2:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:11][CH2:12][CH2:13][CH2:14][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 10061000HCID 10061000, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Hydroxyacetophenone (13.6 g.), 1,3-dibromopropane (121.2 g.) and potassium carbonate (15.8 g.) were dissolved in acetone (250 ml.), and the solution was refluxed under heating for 6 hours. After the reaction mixture was filtered, the acetone was removed by evaporation from the filtrate under reduced pressure to give an oily residue. The excess of 1,3-dibromopropane was removed by distillation from the oily residue under reduced pressure to give a residue, which was subjected to column chromatography on silica gel (20 g.). Elution was carried out with benzene and the fractions containing a desired compound were collected. The eluate was evaporated to dryness under reduced pressure to give p-(3-bromopropoxy)acetophenone (18 g.).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 6 hours
  3. filtrationAfter the reaction mixture was filtered
  4. customthe acetone was removed by evaporation from the filtrate under reduced pressure
  5. customto give an oily residue
  6. customThe excess of 1,3-dibromopropane was removed by distillation from the oily residue under reduced pressure
  7. customto give a residue, which
  8. washElution
  9. additionthe fractions containing a desired compound
  10. customwere collected
  11. customThe eluate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c8365c8601ba4b9da2e0285c323cf354
Source dataset
uspto-grants-1980_12
Patent number
US04237305

Reaction notes

Loading…