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ChemicalBook CAS DataBase List 4-isopropoxy-3-(trifluoroMethyl)benzoic acid
213598-16-4

4-isopropoxy-3-(trifluoroMethyl)benzoic acid synthesis

6synthesis methods
-

Yield:213598-16-4 96%

Reaction Conditions:

Stage #1: 4-isopropoxy-3-(trifluoromethyl)benzonitrilewith water;sodium hydroxide in ethanol at 80; for 18 h;
Stage #2: with hydrogenchloride in water;

Steps:

1.1.B

To a solution of 4-isopropoxy-3-(trifluoromethyl)benzonitrile (183 g, 798 mmol) in EtOH (1 L) was added 5 N NaOH (559 mL, 2.80 mol). The reaction mixture was heated to 80 °C for 18 h. Volatiles were removed in vacuo and 3 N HCl was added until the mixture was acidic. A precipitate formed that was collected by vacuum filtration. The solid was washed with water and hexanes. The solid was dissolved in EtOAc and dried over MgS04 to give 4-isopropoxy-3- (trifluoromethyl)benzoic acid (191 g, 770 mmol, 96% yield) as a white solid. Exact mass calculated for 248.1, found: LCMS m/z = 249.3, [M+H+]; lU NMR (400 MHz, CDC13) δ ppm 1.41 (d, = 6.0 Hz, 6 H), 4.76 (sep, = 6.0 Hz, 1 H), 7.05 (d, = 8.8 Hz, 1 H), 8.22 (dd, Jx = 8.8, J2 = 2.2 Hz, 1 H), 8.33 (d, = 2.0 Hz, 1 H).

References:

WO2011/109471,2011,A1 Location in patent:Page/Page column 111