Nitromethane → 3,4-Dimethoxy-beta-nitrostyrene

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Reaction Steps

According to Scheme I, an optionally substituted dimethoxybenzaldehyde of formula 2, nitromethane and a catalystic amount of ammonium acetate (about 10 mol% per dimethoxybenzaldehyde) are heated to about 70°-100° C. for about 2-6 hours. The resulting product is precipitated from a mixture of water and isopropanol (about 7:1) to yield a nitrostyrene derivative of formula 3 (step 1). For example, 3,4-dimethoxybenzaldehyde is treated with NH4OAc and nitromethane to yield 3,4-dimethoxy-β-nitrostyrene (3). Alternatively, one can purchase 3,4-dimethoxy-β-nitrostyrene commercially.

Provenance & Evidence