This invention provides a process for producing an epoxy compound industrially advantageously at low cost in a short process. Furthermore, this invention provides a novel fruity, camphoric, floral, amber or woody fragrance-, flavor- or scent-imparting composition containing said epoxy compound, and foods & drinks, perfumes, cosmetics and tobaccos containing said composition.
In this invention, the epoxy compound can be produced by letting an a-halocyclododecanone represented by the following general formula (1)
(where X1 denotes chlorine, bromine or iodine) and an organic magnesium compound represented by the following general formula (2)
R1MgX1 (2)
(where R1 denotes an alkyl group with 1 to 5 carbon atoms, alkenyl group with 2 to 5 carbon atoms or alkynyl group with 2 to 5 carbon atoms, and X1 denotes chlorine, bromine or iodine) react with each other for Grignard reaction, hydrolyzing to obtain a halohydrin represented by the following general formula (3)
(where R1 denotes an alkyl group with 1 to 5 carbon atoms, alkenyl group with 2 to 5 carbon atoms or alkynyl group with 2 to 5 carbon atoms; X1 denotes chlorine, bromine or iodine; and the wavy line denotes cis form, trans form or a mixture consisting of cis form and trans form), and letting the halohydrin and a base react with each other in the presence of an phase transfer catalyst or adding an aprotic polar solvent for reaction.
本发明提供了一种工业化生产环
氧化合物的工艺,该工艺成本低,流程短。此外,本发明还提供了一种含有所述环
氧化合物的新型果味、
樟脑味、花香、琥珀香或木香的
香料、香精或香味诱导组合物,以及含有所述组合物的食品和饮料、香
水、化妆品和烟草。
在本发明中,环
氧化合物可以通过以下通式(1)代表的 a-卤代
环十二酮来生产
(其中 X1 表示
氯、
溴或
碘)和由以下通式(2)表示的
有机镁化合物
R1MgX1 (2)
(其中 R1 表示具有 1 至 5 个
碳原子的烷基、具有 2 至 5 个
碳原子的
烯基或具有 2 至 5 个
碳原子的炔基,X1 表示
氯、
溴或
碘)相互反应,进行格氏反应,
水解得到由以下通式(3)表示的卤代醇
(其中 R1 表示 1 至 5 个
碳原子的烷基、2 至 5 个
碳原子的
烯基或 2 至 5 个
碳原子的炔基;X1 表示
氯、
溴或
碘;波浪线表示顺式、反式或由顺式和反式组成的混合物),让卤代醇和碱在相转移
催化剂存在下相互反应,或加入非沸腾极性溶剂进行反应。