3-Chloro-d-camphor
Title: 3-Chloro-d-camphor
CAS Registry Number: 508-29-2
CAS Name: 3-Chloro-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
Additional Names: 3-chloro-d-2-bornanone
Molecular Formula: C10H15ClO
Molecular Weight: 186.68
Percent Composition: C 64.34%, H 8.10%, Cl 18.99%, O 8.57%
Literature References: Of the two isomers, the endo-form is more stable than the exo-form: Cookson, J. Chem. Soc. 1954, 282. Prepn of endo-form: Kipping, Pope, ibid. 63, 548 (1893). Prepn of exo-form by isomerization of endo-form: Lowry, Steele, ibid. 107, 1382 (1915). uv spectra: Lowry, Owen, J. Chem. Soc. 129, 606 (1926). Crystal structure of endo-form: Wiebenga, Krom, Rec. Trav. Chim. 65, 663 (1946). Configuration: Cookson, loc. cit.; Kumler et al., J. Am. Chem. Soc. 83, 2711 (1961). Review: The Terpenes vol. II, J. L. Simonsen, Ed. (University Press, Cambridge, 2nd ed., 1949) p 397.
 
Derivative Type: endo-Form
Additional Names: a-Chloro-d-camphor; 3a-chloro-d-camphor; camphor monochlorated
Properties: Monoclinic prisms from alc, mp 94°. Volatile with steam. [a]D +96.2° (c = 5 in alc). Practically insol in water. Sol in alcohol, chloroform, ether. uv max (cyclohexane): 305 nm (log e 1.72).
Melting point: mp 94°
Optical Rotation: [a]D +96.2° (c = 5 in alc)
Absorption maximum: uv max (cyclohexane): 305 nm (log e 1.72)
 
Derivative Type: exo-Form
Additional Names: -Chloro-d-camphor; 3b-chloro-d-camphor
Properties: Crystals from alc, mp 117°. [a]D +35° (c = 5 in alc). Readily sol in all ordinary solvents, except water and formamide. Much more sol in 96% alc than endo-form. On standing, loses HCl. uv max (cyclohexane): 306 nm (log e 1.75).
Melting point: mp 117°
Optical Rotation: [a]D +35° (c = 5 in alc)
Absorption maximum: uv max (cyclohexane): 306 nm (log e 1.75)

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