Sodium Hydroxide → 2-hydroxy-6-(trifluoromethyl)benzaldehyde
Reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH:4]=[O:5].[OH-:14].[Na+]>>[OH:14][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH:4]=[O:5]Participants
3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-fluoro-6-trifluoromethylbenzaldehyde (25 g) and aqueous sodium hydroxide solution (0.5 M; 866 ml) was stirred and heated at 80° C. under nitrogen for 43 hours. The cooled solution was washed with ether (2×350 ml), acidified with concentrated hydrochloric acid, then extracted with ether (2×500 ml). The combined extracts were dried over magnesium sulphate and the solvent removed in vacuo. The residue was purified by flash chromatography over silica eluting with a 95:5 mixture of dichloromethane and methanol. Appropriate fractions were combined and the solvent removed in vacuo to give 2-hydroxy-6-trifluoromethylbenzaldehyde (6.2 g) as an oil.
Workup
- washThe cooled solution was washed with ether (2×350 ml)
- extractionextracted with ether (2×500 ml)
- dry with materialThe combined extracts were dried over magnesium sulphate
- customthe solvent removed in vacuo
- customThe residue was purified by flash chromatography over silica eluting with a 95:5 mixture of dichloromethane and methanol
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-8a05c832265c4800b750e75a59017c67
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935973
Reaction notes
Loading…