1-(3-Fluoro-4-methylphenyl)ethanol → 1-(3-Fluoro-4-methylphenyl)ethan-1-one
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
Product 1
Reagents, catalysts & solvents 1
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 to yield the title compound as a pale yellow oil (47.5 mg, 86.0%).
Workup
- filtrationThe reaction mixture was filtered through Celite
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-0498ef0e78694a75a5377ea196575744
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087606B2
Reaction notes
Loading…