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

HRID 1794506

Reaktionsgleichung

Reaktionsgleichung von HRID 1794506
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

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)+

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-95c1a4a8b4a6429681379e0440250617
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022733B2

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