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

HRID 324582노트

반응식

HRID 324582 반응식
[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

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 102792-AcetylhydroquinoneHCID 11430Potassium Carbonate

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-8f12717ac52842b189558e437b43a36b
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218427B1

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