Methanol → Ethanedial, 1,2-bis(2,2-dimethylhydrazone)

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Reaction Steps

1,1-Dimethylhydrazine (3.20 ml, 41.9 mmol) was added to a mixture of MeOH (14 ml) and a 40 wt % glyoxal solution (2.40 ml, 20.9 mmol) in water at 0° C. The resulting mixture was stirred for 24 h at room temperature. The mixture was then dried over Na2SO4, filtered, and concentrated under vacuum to afford glyoxal bis(N,N-dimethylhydrazone) (abbreviated as bis-hydrazone A) as an orange-brown oil (2.78 g, 94% yield). The 1H NMR data (CDCl3, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 7.13 (singlet, 2 H), 2.89 (singlet, 12 H). The 13C NMR data (CDCl3, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 134.9, 43.1. From the 1H NMR and 13C NMR data, the structure of the product was determined to be as follows:

Provenance & Evidence