4'-Hydroxyacetophenone → 1-(4-(2-Bromoethoxy)phenyl)ethanone

HRID 273483Notes

Reaction equation

HRID 273483 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[Br:17][CH:18](Br)[CH3:19]>CC(C)=O>[Br:17][CH2:18][CH2:19][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 112011,1-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 234408111-(4-(2-Bromoethoxy)phenyl)ethanoneYield 20%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxyacetophenone (20 g, 147 mmol) and potassium carbonate (81 g, 588 mmol) was placed into 2 L round bottomed flask and acetone (1 L) was added. To this reaction mixture dibromoethane (38 mL) was added in one portion, and then the reaction mixture was allowed to reflux for 36 hours, under nitrogen atmosphere. The reaction mixture was cooled to room temp, and filtered off, residue was washed with acetone (2×100 mL), and the filtrates were combined and concentrated under reduced pressure. The crude was chromatographed over silica gel by using 10-15% ethyl acetate/pet. ether (2 L), affording the title compound 7 g (20%) as a white solid. Mp. 58-61° C.

Workup

  1. customwas placed into 2 L round bottomed flask
  2. temperatureto reflux for 36 hours, under nitrogen atmosphere
  3. filtrationfiltered off
  4. washresidue was washed with acetone (2×100 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was chromatographed over silica gel

Sources & evidence

ORD record
ord-1ab554d7479647e88dbd044250e83810
Source dataset
uspto-grants-2008_11
Patent number
US07456288B2

Reaction notes

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