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Despite the complex setup that Jarrod Sage used to run this reaction, he ended up holding a flask lined with a pattern of crystals consisting mostly of plain old sodium chloride. Sage, an undergraduate at Western Washington University, used this air-tight flask and a glove box to make an oxygen-sensitive molecule for his green catalysis research. He mixed resorcinol with sodium hydride and added that to di-tert-butylchlorophosphine. One of the reaction products was the molecule Sage wanted. But these crystals containing sodium chloride—which isn’t soluble in the organic solvent used in the reaction—built up on the vessel’s walls as a by-product.
Submitted by Jarrod Sage
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