Benzaldehyde, 4-(diphenylamino)- → Benzenamine, 4-ethenyl-N,N-diphenyl-

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Reaction Conditions

Reaction Steps

In a two necked flask, under argon atmosphere, 22.18 g (54.87 mmol) of methyl(triphenyl)phosphonium iodide are dissolved in 100 mL of freshly distilled tetrahydrofuran (THF). After the mixture is cooled to the temperature of 0° C., 1.5 eq. (6.16 g) of potassium tert-butoxide are incorporated. After 30 min of stirring at 0° C., a solution of 4-(N,N-diphenylamino)-benzaldehyde (10 g, 36.80 mmol) in 30 mL of THF is added to the mixture, drop by drop. The temperature of the medium is then left to return to ambient temperature and the stirring continued for 4 additional hours. The medium is then hydrolysed with a saturated sodium carbonate solution then extracted in dichloromethane. The organic phase is washed successively with water, a saturated NaCl solution then dried on Na2SO4. After filtration and evaporation, the crude product is purified on chromatography column on silica [eluent—hexane/ethyl ether: 80/20].

Provenance & Evidence