Cornforth reagent → 1-(4-Methoxy-2,5-dimethylphenyl)ethanone

HRID 1619163Notes

Reaction equation

HRID 1619163 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH:10]([OH:12])[CH3:11])=[C:5]([CH3:13])[CH:4]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10](=[O:12])[CH3:11])=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 2113498354119-38-9

Product 1

HCID 149071491-(4-Methoxy-2,5-dimethylphenyl)ethanoneYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.8 g (4.1 mmol) of 1-(4-methoxy-2,5-dimethylphenyl)ethanol obtained in Step 1 in 30 mL of dichloromethane was reacted with 3.0 g (8.2 mmol) of pyridinium dichromate at room temperature for 2 hours with stirring, followed by filtration through celite. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to afford 1-(4-methoxy-2,5-dimethylphenyl)ethanone as a brown oil (0.54 g, yield: 69%).

Workup

  1. filtrationfollowed by filtration through celite
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-1b1bd11c462f47f8a09a0f1e5a7997ba
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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