Acetovanillone → 1-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

HRID 7472

反応式

HRID 7472 の反応式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)=[O:3].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([O:11][CH3:12])[CH:5]=1)=[O:3]

参加物

6

反応物 3

HCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

生成物 1

HCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanone収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The starting material, 4-benzyloxy-3-methoxyacetophenone, was obtained by heating a solution of 4-hydroxy-3-methoxyacetophenone (20 g, 0.12 mol), benzyl bromide (15.7 ml, 0.13 mol) and potassium carbonate (49.8 g, 0.36 mol), in DMF (400 ml) at 40° C. overnight. After cooling, the mixture was diluted with water, acidified to approximately pH3 and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using petroleum ether/ethyl acetate (8/2 followed by 65/35) as eluent to give 4-benzyloxy-3-methoxyacetophenone (30.3 g, 99%).

後処理

  1. customat 40° C.
  2. customovernight
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-5361ab59f70448ae8738fc7abac188e4
出典データセット
uspto-grants-2006_08
特許番号
US07087602B2

関連ノート

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