Methanol → Methyl 4-chloro-3-(trifluoromethyl)benzoate
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.[CH3:20]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:20])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]Participants
4
Procedure
To a solution of 4-chloro-3-(trifluoromethyl)benzoic acid (10.37 g, 46.2 mmol) in methanol (100 mL) was added concentrated sulfuric acid (0.51 mL, 9.24 mmol). The mixture was heated under reflux overnight. The mixture was allowed to cool to room temperature and concentrated under reduced pressure to form a solid. The solid was filtered and washed with water. The solid was then stirred with saturated aqueous sodium bicarbonate solution to remove any residual sulfuric acid, filtered and dried under vacuum to give the title compound as a white solid (10.18 g). 1H NMR (400 MHz, CDCl3) δ ppm 3.96 (s, 3H), 7.60 (d, J=8.34 Hz, 1H), 8.14 (dd, J=8.34, 2.02 Hz, 1H), 8.37 (d, J=2.02 Hz, 1H).
Workup
- temperatureThe mixture was heated
- temperatureunder reflux overnight
- concentrationconcentrated under reduced pressure
- customto form a solid
- filtrationThe solid was filtered
- washwashed with water
- customto remove any residual sulfuric acid
- filtrationfiltered
- customdried under vacuum
Sources & evidence
- ORD record
- ord-aefca7bd3e3948499b80a87a5c39a1f2
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853419B2
Reaction notes
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