1-(4-Bromo-3,5-dimethoxyphenyl)propan-1-ol → 1-(4-Bromo-3,5-dimethoxyphenyl)propan-1-one

HRID 2359244Notes

Reaction equation

HRID 2359244 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]([OH:13])[CH2:11][CH3:12])=[CH:4][C:3]=1[O:14][CH3:15]>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:4][C:3]=1[O:14][CH3:15]

Participants

4

Reactant 1

HCID 584320031-(4-Bromo-3,5-dimethoxyphenyl)propan-1-ol

Product 1

HCID 584320651-(4-Bromo-3,5-dimethoxyphenyl)propan-1-oneYield 100.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-3,5-dimethoxyphenyl)propan-1-ol (5.4 g, 19.6 mmol) in anhydrous CH2Cl2 (75 mL) was added MnO2 (17 g, 196 mmol). After the mixture was placed under a drying tube and stirred at room temperature for 22 hrs, 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)propan-1-one as a white solid (5.4 g, 100% 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-d286580f32f642b394c1b0f7f44a6c40
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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