Hydrochloric Acid → HCID 59987958, compound

Temperature

0 °C

DMF (10 mL) was added to a reaction vessel containing 4-formyl-benzoic acid methyl ester (501.1 mg, 3.053 mmol) and potassium acetate (15.0 mg, 0.153 mmol), and the mixture was cooled to 0° C. Trimethyl(trifluoromethyl)silane (0.96 mL, 6.105 mmol) was added dropwise and the mixture was stirred for 50 minutes. 2 N hydrochloric acid (10 mL) was then added to the reaction mixture, and the mixture was stirred at room temperature overnight and then diluted with ethyl acetate. A saturated aqueous sodium bicarbonate solution was added, and the organic layer and the aqueous layer were separated. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-(2,2,2-trifluoro-1-hydroxy-ethyl)-benzoic acid methyl ester (680.8 mg, 95%).

1. stirringthe mixture was stirred at room temperature overnight
2. customthe organic layer and the aqueous layer were separated
3. washThe organic layer was sequentially washed with water and saturated brine
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-8255ad144fdd4e6980833baca9cf229f

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2