Dimethoxy4ethoxybenzaldehyde [8 from syringaldehyde

A well-stirred suspension of 21.9 g syringaldehyde in 45 mL H20 was heated to reflux in a heating mantle. There was then added a solution of 15 g NaOH in 60 mL H20. The heating and stirring was continued until the generated solids redissolved. Over a period of 10 min, there was added 23 g diethyl sulfate, then refluxing was continued for 1 h. Four additional portions each of 5 g diethyl sulfate and of 6 mL 20% NaOH were alternately added to the boiling solution over the course of 2 h. The cooled reaction mixture was extracted with Et20, the extracts pooled and dried over anhydrous MgSO*, decolorized with Norite, and stripped of solvent. The crude 3,5-dimethoxy-4-ethoxy-benzaldehyde weighed 21.8 g and melted at 51-52°C.

See the same reference in Pihkal for details on how to use ethyl iodide instead of diethyl sulfate.

[2] Synthesis, 308(1983)

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