4'-Hydroxyacetophenone → 1-[4-(2-Phenylethoxy)phenyl]ethanone

HRID 1632242Notes

Reaction equation

HRID 1632242 reaction equation
[CH2:1](Br)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7666Phenethyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 133400571-[4-(2-Phenylethoxy)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 18.5 g. of phenethylbromide, 20.4 g. of p-hydroxyacetophenone, 17.3 g. of anhydrous potassium carbonate and 150 ml. of acetone was refluxed under argon for 22 hours. The reaction was then cooled and partitioned between ether and water. The ether layer was washed with water and then extracted with two 100 ml. portions of cold 1N sodium hydroxide. These extracts were combined, washed with water and brine, dried and evaporated to an oil. The oil was purified by chromatography, giving the desired intermediate as a light yellow oil.

Workup

  1. additionA stirred mixture of 18.5 g
  2. temperatureThe reaction was then cooled
  3. custompartitioned between ether and water
  4. washThe ether layer was washed with water
  5. extractionextracted with two 100 ml
  6. washwashed with water and brine
  7. customdried
  8. customevaporated to an oil
  9. customThe oil was purified by chromatography

Sources & evidence

ORD record
ord-b6f6c19a5129447787131047731252e0
Source dataset
uspto-grants-1984_10
Patent number
US04474809

Reaction notes

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