Anisole → Desoxyanisoin
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]([CH2:17][C:18](Cl)=[O:19])=[CH:13][CH:12]=1>>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:18](=[O:19])[CH2:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:3][CH:2]=1Participants
Procedure
1-(4-Methoxyphenyl)-2-(4-methoxyphenyl)ethanone was prepared from anisole and 4-methoxyphenylacetyl chloride (prepared by heating the commercially available carboxylic acid in thionyl chloride and subsequent concentration) using the method described in step A of Example 9. After step A, the product was chromatographed on silica gel using 3:2 hexane/EtOAc as eluant. 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone was converted to the title compound following the procedures described in steps C-E of Example 1, except for the following modifications: 1) in step C, the acidic hydrolysis reaction, after dilution with H2O, was extracted 2× with Et2O prior to basification, extraction 3× with EtOAc and isolation of the desired amine after concentration; and 2) the prep HPLC purification of step D utilized 65% solvent B as eluant.
Workup
- customprepared
- temperatureby heating
- concentrationthe commercially available carboxylic acid in thionyl chloride and subsequent concentration)
- customAfter step A, the product was chromatographed on silica gel using 3:2 hexane/EtOAc as eluant
- custom1) in step C, the acidic hydrolysis reaction
- extractionafter dilution with H2O, was extracted 2× with Et2O
- extractionto basification, extraction 3× with EtOAc and isolation of the desired amine
- concentrationafter concentration
- customand 2) the prep HPLC purification of step D
Sources & evidence
- ORD record
- ord-ac204207c2f440809300453f10f53cd1
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776983
Reaction notes
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