Dichloromethane → 1-(4-Chloro-3,5-dimethoxyphenyl)ethanone
Reaction equation
[C:1]([O:4][C:5]1C2C=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14]([O:16]CC)=O)[CH:6]=1)(=O)C.O.[CH:20]([Cl:23])(Cl)Cl.Cl[CH2:25]Cl>[O-2].[O-2].[Mn+4]>[Cl:23][C:20]1[C:9]([O:13][CH3:12])=[CH:8][C:7]([C:14](=[O:16])[CH3:25])=[CH:6][C:5]=1[O:4][CH3:1]Participants
5
Conditions
- Temperature
- 40 °C
Procedure
To a solution of the compound obtained in the above (1) (1.23 g) in dichloromethane 928 mL) was added 85% activated manganese dioxide (5.81 g), and the mixture was stirred at 40° C. for 4 hours. The reaction solution was cooled to room temperature, and then thereto was added water-chloroform, and an insoluble was filtered off through Celite, and then the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1→1/1) to give 1-(4-chloro-3,5-dimethoxyphenyl)ethanone [REx(22-2)] (723 mg) as a colorless powder.
Workup
- additionwas added 85%
- temperatureThe reaction solution was cooled to room temperature
- filtrationan insoluble was filtered off through Celite
- customthe organic layer was separated
- concentrationThe organic layer was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1→1/1)
Sources & evidence
- ORD record
- ord-de2af95c4b6c4f83a96ed7c2c492c8e9
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278944B2
Reaction notes
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