Safe Execution of a Large-Scale Ozonolysis:  Preparation of the Bisulfite Adduct of 2-Hydroxyindan-2-carboxaldehyde and Its Utility in a Reductive Amination

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...

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Bibliographic Details
Published in:Organic process research & development 2003-03, Vol.7 (2), p.155-160
Main Authors: Ragan, John A, am Ende, David J, Brenek, Steven J, Eisenbeis, Shane A, Singer, Robert A, Tickner, Derek L, Teixeira, John J, Vanderplas, Brian C, Weston, Neil
Format: Article
Language:English
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Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/op0202235