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.
CITATION STYLE
Ragan, J. A., Am Ende, D. J., Brenek, S. J., Eisenbeis, S. A., Singer, R. A., Tickner, D. L., … Weston, N. (2003). 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 and Development, 7(2), 155–160. https://doi.org/10.1021/op0202235
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