8160. Retene

Nomenclature

CAS number: 483-65-8
1-Methyl-7-(1-methylethyl)phenanthrene.
C18H18; mol wt 234.34.
C 92.26%, H 7.74%.

Description and references

Occurs in pine tar, in fossilized pine, in high-boiling tar oils. Formed by Se or Pd dehydrogenation of abietic acid: Ruzicka, Waldmann, Helv. Chim. Acta 16, 842 (1933). Synthesis starting with methyl β-(6-isopropyl-2-naphthoyl)propionate: Bardhan, Sengupta, J. Chem. Soc. 1932, 2520, 2798; cf. Bogert, Science 77, 289 (1933). Review and bibliography: Fieser, Fieser, Natural Products Related to Phenanthrene (New York, 3rd ed., 1949).

Chemical structure

Properties

Plates, scales from alc, mp 99°. bp10 208°; bp760 390-394°. Absorption spectrum: Askew, J. Chem. Soc. 1935, 509. Insol in water. Sol in hot alcohol, benzene, hot ether, carbon disulfide. Upon treatment with CrO3 in acetic acid forms retenequinone, C18H16O2, mp 197.5°.