From citronellal (1) as the parent substance, citronellyl acetal (4), geranyl acetal (5) and a mixed acetal (6) of citronellol (2) and geraniol (3) were synthesized.
Alkyl vinyl ether (10), which is derived from saturated acetals (8) of (4), (5) and (6), and the respective saturated ether (11) were also synthesized. When (4), (5) and (6) were decomposed with H
2SO
4, H
3PO
4 and HCOOH, under cooling the original (1), (2), and (3) were obtained.
In a same fashion, dihydrocitronellol (7) and dihydrocitronellal (9) were obtained from (8). Dihydrocitronellol (7) was also obtained when hydro-decomposition of (4), (5), (6), and (8) was carried out.
The acetals (4), (5), (6), and (8) have a mild hydroxycitronellal-like odor, by above 200°C/1 mmHg ; conceivably these can be used as a stable perfume which has little skin irritation.
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