5128. Isoborneol

Nomenclature

CAS number: 124-76-5
(1R,2R,4R)-rel-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol; exo-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol; exo-2-bornanol; exo-2-camphanol; (±)-isoborneol; dl-isoborneol.
C10H18O; mol wt 154.25.
C 77.87%, H 11.76%, O 10.37%.

Description and references

Prepn: Pickard, Littlebury, J. Chem. Soc. 91, 1973 (1907); Truett, Moulton, J. Am. Chem. Soc. 73, 5913 (1951) DOI; Ziegler, GB 803178 (1958). Resolution: Pickard, Littlebury, loc. cit.; Kenyon, Priston, ibid. 127, 1472 (1925). Prepn of the (1R,2R,4R)-form by reduction of d-camphor with lithium aluminum hydride: Trevoy, Brown, J. Am. Chem. Soc. 71, 1675 (1949) DOI. Configuration (isoborneol = exo-form; borneol = endo-form): Toivonen et al., Acta Chem. Scand. 3, 991 (1949) DOI. Separation of isoborneol from borneol via the p-nitrobenzoate deriv: Truett, Moulton, loc. cit. Review: J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 2nd ed., 1949) pp 365-367; A. R. Pinder, The Chemistry of the Terpenes (Chapman & Hall, London, 1960) pp 22-24, 101, 103, 105-107, 111.

Chemical structure

Properties

Crystals from petr ether. Sublimes on heating, mp 212° (in a sealed tube). Practically insol in water. Readily sol in alcohol, ether, chloroform.

Derivative

(1S,2S,4S)-Form.

Nomenclature

CAS number: 16725-71-6
(+)-isoborneol; d-isoborneol.

Properties

Crystals from petr ether, mp 214°. Approx [α]D +34.3° in alc soln: Picard, Littlebury, loc. cit.

Derivative

(1R,2R,4R)-Form.

Nomenclature

CAS number: 10334-13-1
()-isoborneol; l-isoborneol.

Properties

Crystals from petr ether, mp 214°. Approx [α]D 34.3° in alc soln.