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Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents.

ABSTRACT: While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl₂ with TPPO precipitates a TPPO-Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and the reliability of the precipitation in the presence of polar functional groups were examined to show the utility and limitations of this method.

SUBMITTER: Batesky DC

PROVIDER: S-EPMC5634519 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents.

Batesky Donald C DC Goldfogel Matthew J MJ Weix Daniel J DJ

The Journal of organic chemistry 20170928 19

While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl<sub>2</sub> with TPPO precipitates a TPPO-Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and ...[more]

PMID: 28956444

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