Diisobutylaluminum hydride → 3-[4-(Trifluoromethyl)phenyl]propanal

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Reaction Conditions

Reaction Steps

The above 3-(4-trifluoromethylphenyl)propionic acid ethylester 81.0 g (329 mmol) was stirred in toluene 500 ml while the temperature was cooled to −60° C., and a 1.01 M of toluene solution 329 ml (332 mmol) of DIBAL was added dropwise, and the mixture was stirred at −55° C. for 15 minutes. At the same temperature, a saturated ammonium chloride aqueous solution 200 ml was added dropwise to the reactant, and the mixture was heated to room temperature and stirred for 30 minutes. Ether 100 ml was added to the reactant, and the mixture was stirred at room temperature for one hour, and magnesium sulfate was added, and the suspension was filtered with cerite. The filtrate was washed with water, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) to obtain 3-(4-trifluoromethylphenyl)propanal 62.5 g (309 mmol). The yield was 93.9% from 3-(4-trifluorophenyl)propionic acid ethylester.

Provenance & Evidence