The invention provides a novel and efficient method for the synthetic preparation of cis-nonen-6-yl chloride which is a useful intermediate compound for the syntheses of, for example, cis-nonen-6-yl acetate, cis-nonen--6-ol, cis-nonen-6-yl and the like as flavors as well as cis-dodecen-9-yl acetate and cis-tetradecen-11-yl acetate known as sexual pheromone compounds of several noxious insects. The inventive method comprises reacting 1-bromo-3-chloropropane with the Grignard reagent of cis-hexen-3-yl chloride which is a chlorination product of cis-hexen-3-ol known by a trivial name of leaf alcohol. The reaction is preferably carried out in tetrahydrofuran in the presence of a catalyst which may be lithium copper dichloride or dilithium copper tetrachloride at 0 to 40°C.
本发明提供了一种合成制备顺式
壬烯-6-酰
氯的新颖而有效的方法,顺式
壬烯-6-酰
氯是一种有用的中间化合物,可用于合成例如作为
香料的顺式
壬烯-6-
乙酸酯、顺式
壬烯-6-醇、顺式
壬烯-6-基等,以及作为几种有害昆虫的性信息素化合物的顺式
十二烯-9-
乙酸酯和顺式十四烯-11-乙酸酯。本发明的方法包括使
1-溴-3-氯丙烷与顺式己烯-3-基
氯的
格氏试剂反应,顺式己烯-3-基
氯是顺式己烯-3-醇的
氯化产物,俗称
叶醇。反应最好在
四氢呋喃中进行,催化剂可以是二
氯化
铜锂或四
氯化二
锂铜,温度为 0-40°C 。