Sodium Hydroxide → 2-Cyclopropyl-4-(trifluoromethyl)benzoic acid
Reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[CH:14]1[CH2:16][CH2:15]1.[OH-].[Na+]>C(O)C>[CH:14]1([C:5]2[CH:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][C:4]=2[C:3]([OH:17])=[O:2])[CH2:16][CH2:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 485 mg (1.986 mmol) 2-cyclopropyl-4-trifluoromethyl-benzoic acid methyl ester in 8 ml ethanol at room temperature, was added 1.99 ml (3.972 mmol) 2N NaOH. The mixture was heated in an 80° C. oil bath for 30 minutes. The solution was cooled to room temperature and the ethanol was evaporated. The residue was diluted with water, acidified with 2N HCl to pH 2 and dichloromethane was added. The aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 0.197 g (27%) of the title compound as a light yellow solid.
Workup
- temperatureThe solution was cooled to room temperature
- customthe ethanol was evaporated
- additionThe residue was diluted with water
- additionwas added
- extractionThe aqueous phase was extracted twice with dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)
Sources & evidence
- ORD record
- ord-f10306c4300d4f55ae068b859d18d2c5
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067911B2
Reaction notes
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