1-(3-Fluoro-4-methylphenyl)ethanol → 1-(3-Fluoro-4-methylphenyl)ethan-1-one

HRID 1348687Notes

Reaction equation

HRID 1348687 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([F:11])[CH:5]=1)[CH3:3].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[F:11][C:6]1[CH:5]=[C:4]([C:2](=[O:1])[CH3:3])[CH:9]=[CH:8][C:7]=1[CH3:10]

Participants

4

Reactant 2

HCID 219913931-(3-Fluoro-4-methylphenyl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 27745691-(3-Fluoro-4-methylphenyl)ethan-1-oneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-hydroxyethyl)-2-fluorotoluene (55.8 mg, 0.36 mmol) in methylene chloride (1 mL) were added molecular sieve 4A (56.0 mg) and PCC 94.0 mg (0.43 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel [silica gel 5 g, hexane/ethyl acetate (10/1)] to yield the title compound as a pale yellow oil (47.5 mg, 86.0%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel [silica gel 5 g, hexane/ethyl acetate (10/1)]

Sources & evidence

ORD record
ord-c5546e3bb9464807b127717147428b0f
Source dataset
uspto-grants-2007_05
Patent number
US07211577B2

Reaction notes

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