Triphenylphosphine → (5-Carboxypentyl)triphenylphosphanium bromide

Participants

Reaction Steps

A mixture of 6-bromohexanoic acid (50 g.), triphenylphosphine (67.1 g.) and 240 ml. of acetonitrile is heated at reflux for 22 hr. Then 160 ml. of acetonitrile is removed by distillation. The solution is cooled and to it is added 240 ml. of benzene. The title compound is obtained as crystals, m.p. 201°-203° C.; infrared spectral absorptions at 2800, 1705, 1585, 1480, 1435, 1375, 1225, 1210, 1190, 1115, 745, 725, and 695 cm.-1 ; and NMR peaks at 1.5-1.9, 2.2-2.6, 3.3-4.0 and 7.7-8.0 (multiplet) δ.

Provenance & Evidence