Aniline → Tetrakis(anilinomethyl)phosphanium chloride

Participants

Reaction Steps

Aniline (7.70 g) was added to a solution of 3.83 g of tetrakis(hydroxymethyl)phosphonium chloride (THPC) in 75 ml of ethanol. There was a mild exotherm, followed immediately by the separation of solids. The mixture was stirred for 2 hours and then filtered, giving 9.15 g (93.0 percent yield) of tetrakis(anilinomethyl)phosphonium chloride, m.p. 129°-130°, as a white crystalline solid that yellowed rapidly on exposure to light. No further solids separated from the filtrate in the next 5 hours. The filtrate and washings, stripped under vacuum, left 1.15 g of a yellow oil containing the remainder of the product and the unreacted aniline.

Provenance & Evidence