4,4'-Dimethoxydiphenylamine → 1,1-bis(p-2,2,2-trifluoroethoxyphenyl)-2-[N,N-bis-(4-methoxyphenyl)amino]ethylene

Participants

Reaction Steps

Using a 30-ml flask similar to that used in Production Example 1, 0.65 g (2.84 mmole) of 4.4'-dimethoxydiphenylamine and 5 mg of p-toluenesulfonic acid monohydrate were added to 10 ml anhydrous toluene solution containing 1.11 g (2.84 mmole) of 1,1-bis(p-2,2,2-trifluoroethoxyphenylacetaldehyde under a nitrogen atmosphere, and refluxed for 3 hours while dehydrating using molecular sieves 4A. After cooling to room temperature, the solution was filtered and the solvent was distilled off. The residue was purified using an alumina column (toluene). The resulting white solid was recrystallized from hexane to yield white crystals of 1,1-bis(p-2,2,2-trifluoroethoxyphenyl)-2-[N,N-bis-(4-methoxyphenyl)amino]ethylene [Compound (4)] in an amount of 1.46 g (yield 85%).

Provenance & Evidence