[3-Chloro-4-(trifluoromethyl)phenyl]methanol → 3-Chloro-4-(trifluoromethyl)benzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH2:5][OH:6]>ClCCCl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])[CH:5]=[O:6]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Step A A mixture of 3-chloro-4-(trifluoromethyl)benzyl alcohol (Synquest) (4.77 g, 23 mmol) and activated MnO2 (19.5 g, 230 mmol) in 1,2-dichlorethane (80 mL) was heated and stirred at 80° C. for 3 h. The mixture was cooled to room temperature and filtered through a short pad of celite. The celite was washed with dichloromethane, and ethyl acetate. The filtrates were combined, concentrated, dried under reduced pressure to give 3-chloro-4-(trifluoromethyl)benzaldehyde as a light yellow oil (2.8 g, 60%).
Workup
- temperaturewas heated
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered through a short pad of celite
- washThe celite was washed with dichloromethane, and ethyl acetate
- concentrationconcentrated
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-86b6bde40e0747a296759688ef21f51e
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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