Methanol → 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acid

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Reaction Conditions

Reaction Steps

Into a 500-mL round-bottom flask, was placed ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate (7 g, 14.59 mmol, 1.00 equiv), methanol (100 mL), water (100 mL), sodium hydroxide (1.75 g, 43.75 mmol, 3.00 equiv). The resulting solution was stirred for 4 h at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 2×50 mL of ethyl acetate and the aqueous layers combined. The pH value of the solution was adjusted to 1-2 with hydrogen chloride aq. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×50 mL of brine. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 5.1 g (77%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid as a light yellow solid.

Provenance & Evidence