Safe Execution of a Large-Scale Ozonolysis: Preparation of the Bisulfite Adduct of 2-Hydroxyindan-2-carboxaldehyde and Its Utility in a Reductive Amination
Organic Process Research & Development2003Vol. 7(2), pp. 155–160
Citations Over TimeTop 25% of 2003 papers
John A. Ragan, David J. am Ende, Steven J. Brenek, Shane A. Eisenbeis, Robert A. Singer, Derek L. Tickner, John J. Teixeira, Brian C. Vanderplas, Neil P. Weston
Abstract
Several routes to bisulfite adduct 2 were explored, the most efficient of which involved vinyl Grignard addition to 2-indanone followed by ozonolysis and workup with aqueous NaHSO3 to effect reduction and bisulfite formation in a single pot. The safety and calorimetry of this ozonolysis reaction was studied, and the safe scale-up to 3 kg of olefin is described. The utility of bisulfite adduct 2 as an aldehyde surrogate in a reductive amination reaction is also described.
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