Benzyl Bromide → 1-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

HRID 2091106Notes

Reaction equation

HRID 2091106 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([C:9](=[O:11])[CH3:10])[CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 102792-AcetylhydroquinoneHCID 11430Potassium Carbonate

Product 1

HCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution (400 mL) of 1-(2,5-dihydroxyphenyl)ethanone (25.0 g) in acetonitrile were added benzylbromide (19.6 mL) and potassium carbonate (25.0 g) at room temperature, and the mixture was heated under reflux for 2 hr. The reaction mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. Saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a solid. The obtained solid was washed with ethanol-isopropyl ether to give the title object compound (31.0 g, 80%) as a yellow-green solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionSaturated aqueous ammonium chloride solution was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give a solid
  11. washThe obtained solid was washed with ethanol-isopropyl ether

Sources & evidence

ORD record
ord-ecebd6a5af8544d0923efc398ed7121a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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