Water → 1,1-Dimethylethyl 2-methyl-5-(trifluoromethyl)benzoate

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Reaction Steps

Potassium tert-butoxide (5.40 g, 48.1 mmol) was added to an ice-cooled solution of 2-methyl-5-trifluoromethylbenzoyl chloride (10.5 g, 47.2 mmol) (manufactured by Apollo Scientific Inc.) in tetrahydrofuran (180 ml) in a small portion and the mixture was stirred for 1 hour. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with a 5% aqueous sodium hydrogencarbonate solution, water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=60/1-20/1) to give tert-butyl 2-methyl-5-(trifluoromethyl)benzoate as a colorless oil (9.90 g, yield: 81%).

Provenance & Evidence