Solvolysis of 5‐bromovanillin to syringaldehyde in the presence of copper as catalyst

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Abstract
Solvolysis of substituted aromatic bromo‐aldehydes such as 5‐bromovanillin and 3,5‐dibromo‐4‐hydroxybenzaldehyde using anhydrous methanolic sodium methoxide was undertaken to produce syringaldehyde, which upon methylation with dimethyl sulphate gives 3,4,5‐trimethoxybenzaldehyde. The latter is an intermediate in the synthesis of trimethoprim, a well known antibacterial drug. The solvolysis was carried out in an agitated autoclave at 120°C, using dimethylformamide as a co‐solvent and metallic copper powder as catalyst. The effects of various parameters such as temperature, period of reaction, speed of agitation, type and loading of catalyst, addition of small amounts of water and concentration of co‐solvent on the conversion to syringaldehyde were examined.