2-Methyl-2-butene → 4-(2,2-Difluoroethoxy)benzoic acid

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Reaction Steps

4-(2,2-Difluoroethoxy)benzaldehyde (2.50 g, 13.4 mmol) prepared in Example 13 (13a) was dissolved in a solution mixture of tert-butanol:water (28 mL, 22:6, V/V). Then, to the resulting mixture were added sodium dihydrogen phosphate dihydrate (2.10 g, 13.4 mmol), 2-methyl-2-butene (6.26 mL, 59.1 mmol), and sodium chlorite (4.25 g, 37.6 mmol). The mixture was stirred at room temperature for 4 hours, and then 2-methyl-2-butene (2.85 mL, 26.9 mmol) and sodium chlorite (1.52 g, 13.4 mmol) were further added thereto. The resulting mixture was further stirred at room temperature for 20 hours, and then a saturated ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give 2.71 g of the title compound (white solid, yield: quantitative).

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