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

反応式

[F:1][C:2]([F:18])([F:17])[C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C(F)(F)F)[C:4]([OH:6])=[O:5].[OH-].[Na+].O>CO>[F:1][C:2]([F:17])([F:18])[CH:3]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]([OH:6])=[O:5]

参加物

反応条件

温度: 90 °C

実験手順

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%).