Sodium Hydroxide → 2-Cyclopropyl-4-(trifluoromethyl)benzoic acid

HRID 39425

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]1

Participants

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. MS (m/e): 229.0 (M−H).

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-513a2865dc3247a8bbc54ea1d3089d65
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524909B2

Linked notes

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