Sodium Hydroxide → 4-(4-Methyl-3-thienyl)-3-(trifluoromethyl)benzoic acid

HRID 1950823Notes

Reaction equation

[OH-].[Na+].[CH3:3][C:4]1[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=2[C:19]([F:22])([F:21])[F:20])=[CH:6][S:7][CH:8]=1>CCO>[CH3:3][C:4]1[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[C:19]([F:22])([F:20])[F:21])=[CH:6][S:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydroxide (5M: 6 mL; 30 mmol; 3 eq.) was added to a solution of methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate (3 g; 10 mmol; 1 eq.) in EtOH (90 mL) and the reaction mixture was stirred at 60° C. for 2 hours. After evaporation of the solvent, the residue was taken up in water (300 mL) and the aqueous phase was washed with ethyl acetate (2×100 mL) then acidified to pH 2 with conc. HCl. The solution was concentrated to ca. 100 mL and extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and concentrated in vacuo to afford the title compound (2.6 g, 91%) as a brown oil.

Workup

customAfter evaporation of the solvent
washthe aqueous phase was washed with ethyl acetate (2×100 mL)
concentrationThe solution was concentrated to ca. 100 mL
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b525ced19acf4ae794332aa8ae082d18
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404676B2

Reaction notes

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