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Dichloromethane → 1-(4-Chloro-3,5-dimethoxyphenyl)ethanone

HRID 922452
Notes
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Reaction equation

HRID 922452 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22418719Chloroform waterHCID 675451626-Benzofurancarboxylic acid, 4-(acetyloxy)-, ethyl ester

Product 1

HCID 683105691-(4-Chloro-3,5-dimethoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

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

  1. additionwas added 85%
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationan insoluble was filtered off through Celite
  4. customthe organic layer was separated
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278944B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes