Chloroform → 4-Phenylbutanoylmethyltriphenylphosphonium chloride

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Reaction Steps

A solution of 1-chloro-2-oxo-5-phenylpentane (6.55 g.) in dry chloroform (30 ml.) was added to a solution of triphenylphosphine (8.7 g.) in dry chloroform (30 ml.) and heated at reflux in an atmosphere of dry nitrogen for 4 hours. The solution was then evaporated under reduced pressure and the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether, to give a white solid. Recrystallisation of this material from a mixture of dichloromethane and diethyl ether gave 4-phenylbutanoylmethyltriphenylphosphonium chloride (11.2 g.) in the form of a white crystalline solid, m.p. 192°-195° C. (Elemental analysis: C, 76.0; H, 6.2%; C29H28ClOP requires: C, 75.9; H, 6.2%; νmax 1110 cm-1, 1445 cm-1, 1490 cm-1, 1695 cm-1).

Provenance & Evidence