从柠檬烯一步合成1-甲基-4-乙酰基-1-环己烯

Synthesis of 1-methyl-4-acetyl-1-cyclohexen from Limonene

以柠檬烯为原料,用N-溴代丁二酰亚胺(NBS)在甲醇中进行C1-C2双键加成取代,然后C8-C9双键用KMnO4/NaIO4进行氧化,再脱去C1-C2取代的基团,使双键复原实现了一步合成1-甲基-4-乙酰基-1-环己烯(1),GC含量为99%,总得率为70%,产物的结构经IR,1HNMR、MS和元素分析证实。

1-methyl-4-acetyl-1-cyclohexen was achieved in one step synthesis from limonene as the starting material by protecting C1 -C2 double with addition and displacement of NBS/CH3OH ,followed by oxidation of C8 - C9 double with KMn04/NaIO4 in acetone and water, and subsequent removal of the oxygen atom with zinc and sodium iodide in acetic acid. The purity of product was 99 % and the over yield was 70%. The product structure was proved by IR. ^1HNMR,MS and elementary analysis.