Anisole → 2-(2,5-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)ethanone

HRID 1794506

反応式

HRID 1794506 の反応式
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[CH2:19][C:20](Cl)=[O:21].[Al+3].[Cl-].[Cl-].[Cl-]>ClC(Cl)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[CH2:19][C:20]([C:4]1[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=1)=[O:21]

参加物

5

反応物 3

HCID 7519AnisoleHCID 596088(2,5-Dimethoxyphenyl)acetyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 3582162-(2,5-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)ethanone収率 58%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

To a cooled solution (0° C.) of anisole (1.3 g, 12.4 mmol) and (2,5-Dimethoxyphenyl)acetyl chloride (2.2 g, 10.3 mmol) in dichloroethane (30 ml) was added AlCl3 (1.6 g, 12.4 mmol) and the reaction was stirred for thirty minutes. The reaction was then quenched with 2N HCl and the organic layer was then separated, dried, and concentrated. The resulting oil was taken up into MeOH and a solid crystallized which was collected by filtration to give a white solid (1.7 g, 58%): Mp=108–111° C.; 1H NMR (CDCl3) δ 8.01 (d, 2 H, J=9.0 Hz), 6.92 (d, 2 H, J=8.8 Hz), 6.80–6.70 (m, 3 H), 4.20 (s, 2 H), 3.86 (s, 3 H), 3.75 (s, 3 H), 3.74 (s, 3 H); MS 287 (M+H)+

後処理

  1. customThe reaction was then quenched with 2N HCl
  2. customthe organic layer was then separated
  3. customdried
  4. concentrationconcentrated
  5. customa solid crystallized which
  6. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-95c1a4a8b4a6429681379e0440250617
出典データセット
uspto-grants-2006_04
特許番号
US07022733B2

関連ノート

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