3-Hydroxyacetophenone → 1-[3-(3-Phenylpropoxy)phenyl]ethan-1-one

HRID 17887

反応式

HRID 17887 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[I-].[Na+]>[C:15]1([CH2:14][CH2:13][CH2:12][O:1][C:2]2[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 84873-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzene

生成物 1

HCID 214224401-[3-(3-Phenylpropoxy)phenyl]ethan-1-one収率 94.4%

試薬・触媒・溶媒 2

HCID 5238Sodium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

3′-Hydroxyacetophenone (6.81 g, 50 mmol) and 1-bromo-3-phenyl propane (11.95 g, 60 mmol) were dissolved in dimethylformamide (70 ml). Then, potassium carbonate (15 g) and sodium iodide (0.5 g) were added thereto and the mixture was allowed to react for 7 hours at 80° C. Ethyl acetate (300 ml) and purified water (200 ml) were further added to the reaction mixture prior to stirring for 30 min. The organic layer extracted with ethyl acetate was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to obtain the title compound (12.0 g, yield 94.2%) as a gel.

後処理

  1. customto react for 7 hours at 80° C
  2. customEthyl acetate (300 ml) and purified water (200 ml)
  3. additionwere further added to the reaction mixture
  4. extractionThe organic layer extracted with ethyl acetate
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

出典と根拠

ORDレコード
ord-4521dbc84ec14ce1a4ca820a0481d911
出典データセット
uspto-grants-2010_06
特許番号
US07741323B2

関連ノート

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