3,3'-Bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4'-oxydianiline → 4,4'-Diaminodiphenyl Ether

Participants

Reaction Steps

The reaction liquid was found by gas chromatography (GC) analysis to contain 59.0% of the target compound, 3,3′-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline, 9.3% of 3-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline, and 28.8% of the total of various imines produced by the reaction of hexafluoroacetone with the amine moiety of 4,4′-oxydianiline. 50 ml of toluene were added to the reaction liquid, followed by heating dissolution. After cooling, the precipitated solid matter was filtered, followed by vacuum drying. 15.2 g of crude 3,3′-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline (yield: 91%; purity: 88.2%) were obtained. This crude product was recrystallized in toluene, thereby obtaining 12.0 g of the target 3,3′-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-4,4′-oxydianiline (yield: 72%; purity: 94.5%).

Provenance & Evidence