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

HRID 324582ノート

反応式

HRID 324582 の反応式
[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

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 102792-AcetylhydroquinoneHCID 11430Potassium Carbonate

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-8f12717ac52842b189558e437b43a36b
出典データセット
uspto-grants-2001_04
特許番号
US06218427B1

反応ノート

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