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

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).

1. stirringThe resulting mixture was further stirred at room temperature for 20 hours
2. customto terminate
3. customthe reaction
4. extractionThe resulting mixture was extracted with ethyl acetate
5. washthe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated

ORD record

ord-cbde1c087ec74f8ba41115beb62c9153

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344029B2