Uses
3,5-Bis(trifluoromethyl)benzaldehyde was used in the synthesis of a series of meso-3,5-bis(trifluoromethyl)phenyl-substituted expanded porphyrins.
Synthesis
The oxidation reaction was carried out in a long-necked, single-necked, round-bottomed flask (50 mL) fitted with a magnet. 5.0 mmol of 3,5-bis(trifluoromethyl)benzyl alcohol and 0.05 mmol of TEMPO were added to the round-bottomed flask, followed by 8 mL of dichloromethane as the reaction solvent, then 0.50 mmol of hydrochloric acid (HCl), and finally 0.5 mmol of nitric acid (HNO3), which was hermetically sealed with the top of the flask in direct communication with an oxygen-filled balloon. The flask was closed and the top of the flask was connected directly to an oxygen-filled balloon. When the reaction is complete, a sample is taken and analyzed by gas chromatography, the reaction liquid is transferred to a dispensing funnel and the flask is carefully washed with methylene chloride to combine the organic solutions. The organic phase was washed with saturated Na2S2O3 aqueous solution and NaHCO3 aqueous solution in turn to remove TEMPO and inorganic salts, the organic layer was dried with anhydrous sodium sulfate, and then rotary evaporation to remove the organic solvent to obtain pure benzaldehyde, yield 95%, GC analysis content of more than 99%.
