On the reaction of cinnamyl alcohol with formaldehyde

Abstract

The add-catalyzed reaction of dnnamyl alcohol with formaldehyde has ken studied. Prom the complex reaction product two m-dioxane derivatives and a triol have been isokted, and their structures have been studied.In a number of recent papers 1) we have described our work on the acid-cataIyzed reaction of formaldehyde with unsaturated compounds possessing a conjugated system of double bonds and an aromatic nucleus.It seemed interesting to study the course of this reaction when reactive groups which do not extend the conjugation *) are introduced into such compounds. since they may cause, by interaction with the normal reaction, the formation of unexpected reaction products and thus open up new synthetic routes.Among compounds of this type, cinnamyl alcohol is particularly interesting, since we may expect its reactivity towards formaldehyde to be of the same order as that of styrene, while its structure seems to be genetically related to the reaction of styrene with formaldehyde (1-111) I However, the reaction I11 can never be realized, because the carbonium ion I1 under any practical conditions is instantaneously