Rose oxide (2-(2'-methyl-1'-propenyl) -4-methyltetrahydropyran) is an important olfactive compound valuable in the art of perfumery and can be produced from citronellol by a variety of synthetic routes. Known routes, however, suffer various disadvantages, such as use of dangerous materials or high temperatures and unsatisfactory yields.
The invention provides a novel synthetic route comprising the steps of:-
(1) anodic alkoxylation of citronellol using as a supporting electrolyte an alkali metal aromatic sulfonate;
(2) dealkoxylation of the resulting 2,6-dimethyl-3- elkoxyoct -1-en-8-ol in the presence of a palladium or nickel complex; and
(3) cyclization of the resulting dehydrocitronellol in the presence of an acid.
High yields of rose oxide can be obtained by this route without the need to employ high temperatures or materials that are difficult to handle.
氧化玫瑰(2-(2'-甲基-1'-
丙烯基) -4-甲基
四氢吡喃)是一种重要的嗅觉化合物,在香
水工艺中具有重要价值,可通过多种合成途径从
香茅醇中提取。然而,已知的方法存在各种缺点,如使用危险材料或高温,以及产量不理想。
本发明提供了一种新型合成路线,包括以下步骤
(1) 使用碱
金属芳香
磺酸盐作为支持电解质,对
香茅醇进行阳极烷氧基化;
(2) 在
钯或
镍络合物存在下,对生成的 2,6-二甲基-3-烷氧基-1-烯-8-醇进行脱烷氧基化反应;以及
(3) 在酸的存在下,将得到的脱氢
香茅醇环化。
通过这种方法可以获得高产率的氧化玫瑰,而无需使用高温或难以处理的材料。