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

HRID 1794506

반응식

HRID 1794506 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-95c1a4a8b4a6429681379e0440250617
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022733B2

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