一种反式-4-羟基-2-壬烯醛的低成本合成方法

A Low Cost Synthesis of(E)-4-Hydroxynon-2-enal

介绍了一种反式-4-羟基-2-壬烯醛的低成本合成方法。由呋喃与甲醇反应,制得的1,1,4,4-四甲氧基-2-丁烯进行选择性水解反应,仅得到单水解产物4,4-二甲氧基-2-丁烯醛,而不产生双水解产物1,4-丁烯二醛,这是此方法可降低成本的关键。4,4-二甲氧基-2-丁烯醛再与戊基溴化镁进行格氏反应得1,1-二甲氧基-4-羟基-2-壬烯,然后在树脂催化下,进行缩醛的酸性水解而得到最终产品反式-4-羟基-2-壬烯醛。总收率为8.7%(从呋喃算起)。产物及中间体结构经1HNMR和13CNMR进行了表征。

The resin-catalyzed selective hydrolysis of 1,1,4,4-tetramethoxybut-2-ene, which was formed from the reaction of methanol and furan ,resulted in the formation of 4,4-dimethoxybut-2-enal only. Key of this low cost technic is that no butendial was found in the hydrolysis product. Addition of pentylmagnesium bromide to 4,4-dimethoxybut-2-enal gave 1,1-dimethoxy-4-hydroxynon-2-ene, resincatalyzed hydrolysis of which afforded the final product （E）-4-hydroxynon-2-enal in overall yield of 8.7% from furan. Structures of the final product and intermediates were characterized by ^1HNMR and ^13CNMR.