2'-(Trifluoromethyl)acetophenone

Chemical Properties

Uses

Synthesis

79756-81-3

17408-14-9

The general procedure for the synthesis of o-trifluoromethylacetophenone using 1-(2-trifluoromethylphenyl)ethanol as starting material was as follows: in a round-bottomed flask, which was pre-dried in an oven, eosin Y (5 mmol), 1-(2-trifluoromethylphenyl)ethanol (1 mmol), and 3 equiv. of TBHP (5.5 M solution in decane, with the solvent being dry acetonitrile (ACN) were added. The resulting mixture was degassed for 15 min and subsequently backfilled with nitrogen. Next, the mixture was irradiated at room temperature (25 °C) using a blue LED lamp (12 W, 455 nm). The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with 15 mL of 10% NaHCO3 solution and extracted with ethyl acetate (EtOAc, 3 × 20 mL). The organic extracts were combined, washed with brine (20 mL), dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum. Finally, the crude product was purified by silica gel column chromatography using ethyl acetate:hexane as eluent to obtain the target product o-trifluoromethyl acetophenone.

References