Paper
Synthesis of 4-Methoxysalicylaldehyde via Selective Monomethylation of 2,4-Dihydroxybenzaldehyde
Published Mar 1, 2012 · Hai-Shan Jin, Li‐Ming Zhang, Zhiqing Yan
Journal of Chemical Research
1
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Abstract
4-Methoxysalicylaldehyde, a naturally occurring product, has a range of industrial applications in the preparation of organic compounds, drugs and therapeutic agents. 4-Methoxysalicylaldehyde can be synthesised via selective monomethylation of 2,4-dihydroxybenzaldehyde in toluene in the presence of NaHCO3 in higher yield using cheaper reagents with little production of dimethylation product compared to previous methods. The location of the methoxyl group was confirmed by conversion to 3-acetyl-7-methoxycoumarin by condensation with ethyl acetoacetate.
Selective monomethylation of 2,4-dihydroxybenzaldehyde in toluene with NaHCO3 provides a higher yield and cheaper reagents for the synthesis of 4-Methoxysalicylaldehyde, with potential industrial applications.
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