羟基酪醇的合成

Synthesis of Hydroxytyrosol

以3,4-二甲氧基苯乙酸为起始原料,制得3,4-二羟基苯乙酸,3,4-二羟基苯乙酸再在SOCl2存在下与甲醇反应制得3,4-二羟基苯乙酸甲酯,以Bouveault-Blanc反应为基本原理,通过钠/乙醇还原3,4-二羟基苯乙酸甲酯制得羟基酪醇,并通过1HNMR、IR、MS等方法对其进行了表征。该文还对影响羟基酪醇收率的原料配比、反应时间、反应温度以及钠/乙醇还原3,4-二羟基苯乙酸甲酯反应的机理进行了研究和探讨。

3,4-Dihydroxyphenylacetic acid was directly given from the starting material 3,4-dimethoxyphenylacetic acid.Methyl 3,4-dihydroxyphenylacetate was obtained from the reaction of 3,4-dihydroxyphenylacetic acid with SOCl2 in methanol.It is the first time that the important natural product hydroxytyrosol was obtained by using sodium/ethanol reduction on the basis of Bouveault-Blanc classic reaction,thus providing a novel synthetic method of hydroxytyrosol.The resulting product was characterized by means of 1HNMR,IR and MS.In addition,the influence of the molar ratio of methyl 3,4-dihydroxyphenylacetate to sodium,reaction time and reaction temperature on the yield of hydroxytyrosol was investigated.The mechanism for the reductive reaction of methyl 3,4-dihydroxyphenylacetate with sodium/reduction was discussed.