4-Methoxyphenol → 1-[4-(4-Chlorophenoxy)-2-propylphenyl]-2-(4-methoxyphenoxy)ethanone

HRID 1172813

Reaction equation

HRID 1172813 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH2:19][CH2:20][CH3:21])=[O:4].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][O:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)=[C:6]([CH2:19][CH2:20][CH3:21])[CH:7]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 574201412-Bromo-1-[4-(4-chlorophenoxy)-2-propylphenyl]ethanone

Product 1

HCID 686927541-[4-(4-Chlorophenoxy)-2-propylphenyl]-2-(4-methoxyphenoxy)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Step 8 (0.50 g, 1.4 mmol), p-methoxyphenol (2.8 mmol) and cesium carbonate (0.91 g, 2.8 mmol) in DMF (10 mL) was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with water. The solvent was evaporated and the residue was purified by chromatography on silica gel to give the title product as an oil.

Workup

  1. washwashed with water
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d0b2a8c484c34129829722107e95272c
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Linked notes

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