Dimethylformamide → p-[(2-Methyl-2-norbornyl]oxy)nitrobenzene

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Reaction Steps

To a solution of 15.6 g. (0.10 mole) of the crude norborneol in 80 ml. DMF and 160 ml. C6H6 there was added 4.21 g. of 56% NaH dispersion. Following 30 minutes heating at reflux, there was added 14.1 g. of p-fluoronitrobenzene. The mixture was then heated for an additional 6 hours, cooled and washed thoroughly with H2O and brine. The residue was chromatographed on 2 L silica gel (elution with 1:1 SSB:C6H6). Those fractions which showed a single spot on tlc were combined to afford 13.5 g. of product as a yellow oil; the NMR is in agreement with the structure.

Provenance & Evidence