Benzyl Bromide → 1-(3-(Phenylmethoxy)phenyl)ethan-1-one

HRID 17882

Reaction equation

HRID 17882 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:10][C:8]1[CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[CH:6][CH:7]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-oneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Hydroxyacetophenone (136.15 g, 1 mol), potassium carbonate (414.63 g, 2 mol), KI (33.2 g, 0.2 mol), and benzyl bromide (171.04 g, 1 mol) were dissolved in acetone and the reaction mixture was refluxed while stirring for 24 hours, followed by washing with brine. The reaction mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3) to obtain 1-(3-benzyloxyphenyl)ethanone (221.8 g, yield 98%) in an oil state.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. washby washing with brine
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-a937d91372ab4537b5a282709eb27a35
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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