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

HRID 1610564Notes

Reaction equation

HRID 1610564 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>[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-hydroxyacetophenone (101 g, 744 mmol) in acetone (1 L) were added potassium carbonate (154 g, 1.12 mol) and benzyl bromide (130 g, 759 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, diluted with water (500 ml) and extracted with ethyl acetate (500 ml×2). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-4:1) to give the objective substance (128 g, 76%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water (500 ml)
  3. extractionextracted with ethyl acetate (500 ml×2)
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-4:1)
  8. customto give the objective substance (128 g, 76%)

Sources & evidence

ORD record
ord-546018740a014de087f149286dac13a7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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