4'-Hydroxyacetophenone → 1-[4-(Benzyloxy)phenyl]ethan-1-one

HRID 1610541Notes

Reaction equation

HRID 1610541 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+].[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:9]=[CH:8][C:7]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-hydroxyacetophenone (25 g, 184 mmol) in acetone (500 ml) were added potassium carbonate (50.7 g, 367 mmol) and benzyl bromide (32 g, 187 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. Recrystallization of the residue from ethyl acetate-hexane gave the objective substance (36.8 g, 89%).

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. customRecrystallization of the residue from ethyl acetate-hexane
  8. customgave the objective substance (36.8 g, 89%)

Sources & evidence

ORD record
ord-bfaf1cd45f104ecab7ae96737bd8cb0f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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