A stereospecific synthesis of 4‐oxo‐2trans‐hexenal

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Abstract
4‐Oxo‐2trans‐hexenal is an odoriferous substance secreted by certain arthropods and it has also been described as present in soyasauce. It was synthesized as follows: reaction of propanal with the Grignard derivative of 1,1‐diethoxy‐2‐propyne to give 1,1‐diethoxy‐4‐hydroxy‐2‐hexyne, and reduction of the acetylenic bond with sodium in liquid ammonia to 1, 1‐diethoxy‐4‐hydroxy‐2trans‐hexene; oxidation with active manganese dioxide and acid hydrolysis gave the title compound in 96% purity (GLC). This synthesis offers a useful alternative to that described in the literature, which gives a mixture of the cis and trans isomers.

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