Nitromethane → 3-Hexanone, 6-nitro-

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Reaction Steps

To ethyl vinyl ketone (90.1 g, 1285 mmol) in 550 mL of methanol and 556 mL (10282 mmol) of nitromethane at −40° C. was added as a steady stream 84 mL (ca. 386 mmol) of 25% methanolic NaOMe. The resultant pale yellow slurry was allowed to warm to rt over 5 h, and was stirred overnight. The mixture was quenched with 300 mL of saturated NH4Cl followed by 250 mL water and 250 mL brine. The mixture was then extracted with CH2Cl2 (250 mL×4). The extracts were treated with MgSO4 and decolorizing carbon, filtered and concentrated to yield 154 g (92%) pale yelow liquid: 1H NMR: δ 4.43 (t, J=6.6 Hz, 2H), 2.56 (t, J=6.6 Hz, 2H), 2.44 (t, J=7.5 Hz, 2H), 2.25 (m, 2H), 1.06 (t, J=7.5 Hz, 3H).

Provenance & Evidence