Benzyl Bromide → 1-[2-(Benzyloxy)phenyl]ethan-1-one

HRID 1767301Notes

Reaction equation

HRID 1767301 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:11]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 5205131-[2-(Benzyloxy)phenyl]ethan-1-oneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2′-hydroxyacetophenone (68.1 g, 0.500 mol), benzylbromide (94.1 g, 0.550 mol) and K2CO3 (103 g, 0.750 mol) in acetone (1.0 L) was heated at reflux, and the stirring was continued overnight. After cooled to room temperature, the mixture was concentrated under reduced pressure. The residue was diluted with water, and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by distillation under reduced pressure to give 1-[2-(benzyloxy)phenyl]ethanone as a colorless oil. (100 g, yield; 88%)

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe separated organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. distillationThe crude product was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-67e654ddfa284d5caee8d8e5908f9965
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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