Nitromethane → HCID 86653766, compound

Participants

Reaction Conditions

Reaction Steps

In a 500 mL round bottom flask was placed 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde (2.5 g, 12 mmol) and ammonium acetate (1.3 g, 17 mmol). The solids were taken up in nitromethane (240 mL), and the mixture warmed to 80° C. for 90 min. After the reaction was complete, volatiles were removed in vacuo, the residue was dissolved in ethyl acetate (200 mL), washed with water and brine (50 mL each), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 3.3 g 1,4-dimethoxy-2,3,5-trimethyl-6-(2-nitrovinyl)benzene as a yellow solid. Further purification was performed by digesting the solid product in cyclohexane for 3 hrs, after which the 2.5 g pure compound 1,4-dimethoxy-2,3,5-trimethyl-6-(2-nitrovinyl)benzene was obtained. 1H NMR (CDCl3, 400 MHz) 8.24 (d, 1H), 7.95 (d, 1H), 3.65 (s, 3H), 3.63 (s, 3H), 2.41 (s, 3H), 2.25 (s, 3H), 2.21 (s, 3H) ppm.

Provenance & Evidence