Synthesis and reaction mechanism of 3-(4-methoxyphenylazo)acrylic acid.

Using 4-methoxylphenylhydra zine hydrochloride (1a) as starting material, 2-[2-(4-methoxyphenyl) hydrazono] acetic acid (2a) was prepared after treatment with 1 equivalent of 2-oxoacetic acid, and 3-(4-methoxyphenyldiazo) acrylic acid (3a) was obtained with 2 equivalents of 2-oxoacetic acid through a novel reaction. The mechanism of reaction was analyzed with the help of charge distribution computation. This suggests that the novel reaction depends on the electronegativity of C9, which can be mainly affected by the substituents of the benzene ring.

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