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

HRID 324582Notes

Reaction equation

HRID 324582 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+]>CC(C)=O>[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 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2′, 5′-Dihydroxyacetophenone (II-1) (15.22 g, 0.100 mol), benzyl bromide (17.96 g, 0.105 mol) and potassium carbonate (14.51 g, 0.105 mol) in acetone (200 ml) were refluxed for 16 h. After the solvent was removed under reduced pressure, water was added and the residue was extracted three times with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate, and the solvent removed under reduced pressure. The residue was purified by chromatography on silica gel (500 g) eluting with ethyl acetate/hexane=1:4 to give compound (II-2) as yellow crystals (20.96 g, 87%) accompanied by a small amount of di-benzyl derivative. The products were used without further purification. NMR(CDCl3): 2.57(3H, s), 5.04(2H, s), 6.92(1H, d, J=8.8), 7.14-7.31(2H, m), 7.34-7.45(5H, m)

Workup

  1. customAfter the solvent was removed under reduced pressure, water
  2. additionwas added
  3. extractionthe residue was extracted three times with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (500 g)
  8. washeluting with ethyl acetate/hexane=1:4

Sources & evidence

ORD record
ord-8f12717ac52842b189558e437b43a36b
Source dataset
uspto-grants-2001_04
Patent number
US06218427B1

Reaction notes

Loading…