P-Phenylenediamine → P-Phenylenediamine

Participants

Reaction Steps

A 100 ml, glass, sealed container (autoclave) was charged with 10.0 g (92.5 mmol) of 1,4-phenylenediamine, 704 mg (3.70 mmol, 4 mol %) of p-toluenesulfonic acid monohydrate, and 40.7 g (185 mmol, 2 equivalents) of hexafluoroacetone trihydrate, and the inside of the system was turned into a nitrogen atmosphere. Then, the temperature increased was started, and the inside temperature of the reaction liquid was set to 110° C. After stirring for 21 hours, the reaction liquid was cooled down. The reaction liquid was found by gas chromatography (GC) analysis to contain 75.5% of the target compound, 1-(2-hydroxyhexafluoro-2-propyl)-2,5-phenylenediamine, 3.6% of 1,4-phenylenediamine, and 20.9% of imines produced by the reaction of hexafluoroacetone with the amine moiety of 1,4-phenylenediamine. 200 ml of water were added to the reaction liquid, and it was cooled down in iced bath. The precipitated solid was filtered and vacuum dried, thereby obtaining 24.7 g (yield: 97%; purity: 78.9%) of crude 1-(2-hydroxyhexafluoro-2-propyl)-2,5-phenylenediamine. This crude product was recrystallized in toluene, thereby obtaining 18.6 g (yield: 73%; purity: 99.4%) of the target 1-(2-hydroxyhexafluoro-2-propyl)-2,5-phenylenediamine.

Provenance & Evidence