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以3,5-二甲氧基苯甲醛、对甲氧基苄醇为原料,经合成硫醚和砜的中间产物,再利用Ramberg-Backlund反应将砜转化为反式碳碳双键,最后脱去甲基获得白藜芦醇。研究探讨了反应条件对硫醚氧化和对Ramberg-Backlund反应的影响。结果表明,在以H2O2-SeO2为氧化剂,CH3OH为溶剂的条件下,硫醚的氧化效果最佳,砜的产率可达82%;在以CCl4-KOH作为卤化试剂,V(正丁醇)∶V(水)=6∶1的正丁醇-水作为溶剂的条件下,Ramberg-Backlund反应的效果最好,反式双键产物的产率为84%。该合成路线总产率为41%。产物及各中间体的结构经1H(13C)NMR、IR和ESI-MS确证。
Starting from 3,5-dimethoxybenzaldehyde and p-methoxybenzyl alcohol, the sulfone was converted to the trans carbon-carbon double bond by the Ramberg-Backlund reaction through the synthesis of the intermediates of thioether and sulfone. Finally, Resorcinol is obtained by demethylation. The effects of reaction conditions on the oxidation of thioethers and the Ramberg-Backlund reaction were investigated. The results showed that the oxidation of thioether was the best with H2O2-SeO2 as oxidant and CH3OH as solvent, yield of sulfone was up to 82%. When CCl4-KOH was used as halogenation reagent, V (n-butanol) : Water (v) = 6: 1 n-butanol-water as the solvent, the Ramberg-Backlund reaction works best, and the yield of the trans double bond product is 84%. The overall yield of this synthetic route was 41%. The structures of the products and intermediates were confirmed by 1H (13C) NMR, IR and ESI-MS.