1-(4-Bromo-3,5-dimethoxyphenyl)ethanol → 1-(4-Bromo-3,5-dimethoxyphenyl)ethan-1-one

HRID 2359148Notes

Reaction equation

HRID 2359148 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]([OH:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14]>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

4

Reactant 1

HCID 582234841-(4-Bromo-3,5-dimethoxyphenyl)ethanol

Product 1

HCID 584320901-(4-Bromo-3,5-dimethoxyphenyl)ethan-1-oneYield 97%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-3,5-dimethoxyphenyl)ethanol (10.8 g, 41.1 mmol) in anhydrous CH2Cl2 (150 mL) was added MnO2 (48 g, 552 mmol). After the mixture was placed under a drying tube and stirred at room temperature for 22 hours, it was filtered through a pad of Celite and silica gel and rinsed with EtOAc. Concentration of the filtrate in vacuo gave 1-(4-bromo-3,5-dimethoxyphenyl)ethanone as a white solid (10.3 g, 97% yield). The product was used without further purification.

Workup

  1. customAfter the mixture was placed under a drying tube
  2. filtrationit was filtered through a pad of Celite and silica gel
  3. washrinsed with EtOAc

Sources & evidence

ORD record
ord-ff7ce6ec8e794e67a676e5509b7ceeba
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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