Thermal Adducts of Myrcene with Methyl Acrylate and Acrylaldehyde and Their Derivatives

Abstract

The thermal addition of methyl acrylate (2) to rnyrcene (1) yieided a (2:3) mixture of two methylacrylate addtrcts, they were is61ated by gas, chromatography (GLC) and were determined to be 1-methoxycarbonyl-3-(4-methyl-3-pept.enyl)-3-qyclohexene, (4), and 1-methoxycarbonyl- 4-(4-methyl-3-pentenyl)-4-cyclohexene (7), , respectively, on the basis of their NMR spectral, data.
On the other hand the thermal addition of acrylaldehyde (3) to tu(1) also afforded a (2:3) mixture of two acrylaldehyde adducts, which were isdlated by GLC and were determined to be 1-formyi-3-(4-:methy1-3-pentenyl)-3-cyc1ohexene(5), and 1-formy1-4-(4-methy1-3-pe:ntenyl)- 4-cYclohexene(8).
The structures were confirmed on the basis of comparisons of their reduction products- with authentic samples of 1-hydroxymethyl-3-(4-methyl-3-pentenyl)-3-cyclohexene-(6) and 1-hydroxymethyl-4-(4-methyl-3-pentenyl)-4-cyclohexene (9).
(4), (5), (7), and (8) had a fresh wood like odor and also (6), (9) and esters of (9), which was derived from saturated lower fatty acids had a mild flowerly odor,