When nopol (2-pinene-methanol) (1) was oxidized with activated manganese dioxide, 10-formy1-2-pinene (3) was obtained.
Homoperillyl alcohol (2) is derived from (1) when (1) was thermally isomerized with the catalyst systems composed of copper and zinc, at 240±5°C under a reduced pressure.
In a similar fashion, homoperillylaldehyde (4) was also obtained when the dehydrogenation of (2) was carried out.
Compounds (2), (3) and (4) have a mild hydroxycitronellal and ionone-like odor, and the esters of (2) have a mild linallylacetate-like odor ; conceivably these can be used as a stable perfume.
Aldehyde (4) was found to give a very sweet oxime, soluble in dil. ethanol.
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