Water → 3,3,3-trifluoro-2-phenylpropanoic acid

Temperature

90 °C

2.9 g (10 millimole) of methyl ester of α,α-bis(trifluoromethyl)phenylacetic acid, 2.5 g (63 millimole) of sodium hydroxide, 3.0 g of water and 3.0 ml of methanol were charged into an eggplant-type flask having a capacity of 100 ml, provided with a marine-type condenser and refluxed at a bath temperature of 90° C. for 6 hours. Methanol was distilled off from the reaction mixture under reduced pressure, and the residue was dissolved in 30 ml of 3N hydrochloric acid and then extracted with ether. The ether layer was dried with anhydrous MgSO4 and then concentrated under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography, using n-hexane/dichloromethane as a mobile phase, whereby 1.26 g of α-(trifluoromethyl)phenylacetic acid was obtained (yield: 62%).

1. customprovided with a marine-type condenser
2. distillationMethanol was distilled off from the reaction mixture under reduced pressure
3. dissolutionthe residue was dissolved in 30 ml of 3N hydrochloric acid
4. extractionextracted with ether
5. dry with materialThe ether layer was dried with anhydrous MgSO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-5b03f446834c4d9e85c13d6a3ccc98d8

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05808132