Safe execution of a large-scale ozonolysis: Preparation of the bisulfite adduct of 2-hydroxyindan-2-carboxaldehyde and its utility in a reductive amination

…, JJ Teixeira, BC Vanderplas, N Weston

Index: Ragan, John A.; Am Ende, David J.; Brenek, Steven J.; Eisenbeis, Shane A.; Singer, Robert A.; Tickner, Derek L.; Teixeira Jr., John J.; Vanderplas, Brian C.; Weston, Neil Organic Process Research and Development, 2003 , vol. 7, # 2 p. 155 - 160

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Citation Number: 33

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 ...