Triphenylphosphine → N-isobutyl acetamidotriphenylphosphonium chloride

Participants

Reaction Steps

To a solution of triphenylphosphine (229.8 g, 876 mmol) in dry benzene (800 ml) was added N-isobutyl-2-chloroacetamide (131 g, 876 mmol) (prepared by standard methods from 2-chloroacetyl chloride and isobutylamine) in dry benzene (100 ml). The solution was heated under reflux, with vigorous stirring, for 8 hours. Upon cooling, colourless needles formed. These were collected by filtration and the filtrate heated under reflux for a further 8 hours. A second batch of the produce was collected. The combined batches were washed with dry ether and dried in vacuo to give 310 g (86% of theory) of N-isobutyl-acetamidotriphenyl-phosphonium chloride as colourless needles.

Provenance & Evidence