Triphenylphosphine → (5-Carboxypentyl)triphenylphosphanium bromide

Participants

Reaction Steps

An intimate mixture of 6-bromohexanoic acid (19.5 g) and triphenylphosphine (26.3 g) was heated at 150° for three hours in a closed flask. After the reaction was cooled, the crude product was dissolved in chloroform (200 mL) and the resulting solution was diluted just to the cloud point with ether. The mixture was stored at 0° C. for several hours, then the solids were collected by filtration, washed with ether and dried in vacuo to yield 41.3 g of (5-carboxypentyl)triphenylphosphonium bromide, mp 197°-198° C. Anal. Calculated for C24H26BrO2P: C, 63.03; H, 5.73; Br, 17.47. Found: C, 63.00; H, 5.76; Br, 17.54.

Provenance & Evidence