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

HRID 1794506Notes

Reaction equation

HRID 1794506 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-95c1a4a8b4a6429681379e0440250617
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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