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

HRID 324582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324582
[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

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 102792-AcetylhydroquinoneHCID 11430Potassium Carbonate

Produkt 1

HCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8f12717ac52842b189558e437b43a36b
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218427B1

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