4'-Hydroxyacetophenone → 1-(4-Propoxyphenyl)ethan-1-one

HRID 485398Notes

Reaction equation

HRID 485398 reaction equation
[CH2:1](Br)[CH2:2][CH3:3].[CH3:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)=[O:7].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH3:5])=[CH:9][CH:10]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2601321-(4-Propoxyphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 12.3 g. of 1-propyl bromide, 13.6 g. of 4-hydroxyacetophenone, 27.6 g. of potassium carbonate and 200 ml. of acetone was refluxed overnight. The mixture was then cooled, filtered, the filtrate concentrated and distilled in a Kugelrohr. The distillate was dissolved in ethyl acetate, treated with charcoal, filtered through diatomaceous earth, concentrated and dried, giving the desired intermediate as an oil.

Workup

  1. additionA mixture of 12.3 g
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. distillationdistilled in a Kugelrohr
  6. dissolutionThe distillate was dissolved in ethyl acetate
  7. additiontreated with charcoal
  8. filtrationfiltered through diatomaceous earth
  9. concentrationconcentrated
  10. customdried

Sources & evidence

ORD record
ord-40fd65a0599a48068e8f0cb5317fac70
Source dataset
uspto-grants-1985_08
Patent number
US04536517

Reaction notes

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