ChemicalBook CAS DataBase List 5-Trifluoromethyl-1-tetralone

5-Trifluoromethyl-1-tetralone synthesis

5synthesis methods

Product Name:5-Trifluoromethyl-1-tetralone
CAS Number:885268-02-0
Molecular formula:C11H9F3O
Molecular Weight:214.18

2-(Trifluoromethyl)-benzenebutanoic acid

899350-21-1

885268-02-0

General procedure for the synthesis of 5-(trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one from 4-(2-(trifluoromethyl)phenyl)butyric acid: 4-(2-(trifluoromethyl)phenyl)butyric acid (246 mg, 1.06 mmol) was dissolved in chlorosulphonic acid (2 mL) at 0 °C, and the reaction mixture was kept stirred for 1 hour at 0 °C. Upon completion of the reaction, the reaction solution was slowly poured into ice water to quench the reaction. The organic phase was extracted with ethyl acetate, and the organic layer was washed sequentially with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution, then dried with anhydrous magnesium sulfate and filtered. The solvent was removed by distillation under reduced pressure to afford the target compound 5-(trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one as a colorless oil (160 mg, 70% yield).1H NMR (CDCl3, 500 MHz) data were as follows: δ 2.16-2.21 (2H, m), 2.70 (2H, dd, J = 6.4, 6.8 Hz), 3.14 (2H, t, J = 6.4 Hz), 7.43 (1H, t, J = 7.8 Hz), 7.83 (1H, d, J = 7.8 Hz), 8.27 (1H, d, J = 7.8 Hz).

899350-21-1
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885268-02-0
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Yield:885268-02-0 70%

Reaction Conditions:

with chlorosulfonic acid at 0; for 1 h;

Steps:

48.C (48C) 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one

(48C) 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-oneTo 4-[2-(trifluoromethyl)phenyl]butanoic acid (246 mg, 1.06 mmol) produced in (48B), chlorosulfonic acid (2 mL) was added at 0° C., and the resulting mixture was stirred at 0° C. for 1 hour.The reaction solution was added to ice water to stop the reaction. The organic matter was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby the objective title compound was obtained as a colorless oily substance (160 mg, yield: 70%).¹H NMR (CDCl₃, 500 MHz): δ2.16-2.21 (2H, m), 2.70 (2H, dd, J=6.4, 6.8 Hz), 3.14 (2H, t, J=6.4 Hz), 7.43 (1H, t, J=7.8 Hz), 7.83 (1H, d, J=7.8 Hz), 8.27 (1H, d, J=7.8 Hz)

References:

US2011/53974,2011,A1 Location in patent:Page/Page column 57-58