4-Aminophenol → 4-(4-Trifluoromethyl-benzyloxy)-phenylamine

Beteiligte Stoffe

Reaktionsschritte

To a solution of p-aminophenol (0.200 g, 1.83 mmol), 4-trifluoromethylbenzyl alcohol (025 ml, 1.83 mmol) and triphenylphosphine (0.529 g, 2.02 mmol) in 5 ml anhydrous tetrahydrofuran was added diethyl azodicarboxylate (0.318 ml, 2.02 mmol). The reaction mixture was stirred overnight at room temperature under nitrogen. It was then diluted with 70 ml ethyl acetate and the resulting solution was washed sequentially with 50 ml saturated aqueous sodium bicarbonate solution, 50 ml water and 50 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The solid residue was purified by flash column chromatography (silica gel, 15 g), eluting with 8:2 hexane/ethyl acetate to yield the title compound as an off-white solid (0.272 g, 55% yield). MS: 284.1 (M+1)

Herkunft & Nachweise