Process for producing cis-4-t-butylcyclohexanol

Details Process for producing cis-4-t-butylcyclohexanol Process for producing cis-4-t-butylcyclohexanol

1997-03-07

1999-01-05

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568832, 568834, C07C 29145

Patent

active

058565906

ABSTRACT:
A process whereby 4-t-butylcyclohexanol with a high content of the cis-isomer, which is useful as a perfume ingredient, can be economically produced on an industrially available scale at a low cost. The process comprises hydrogenating 4-t-butylcyclohexanone by using a specific ruthenium-phosphine complex as a catalyst in the presence of a base containing an alkali metal and an alkylenediamine having from 1 to 6 carbon atoms.

REFERENCES:
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patent: 5107038 (1992-04-01), Weinstein
patent: 5160498 (1992-11-01), Weinstein
J Org Chem "Stereoselective Hydrogenation of Simple Ketones Catalyzed by Ruthenium (II) Complexes", Ohkuma, 61 pp. 4872-4873, Aug. 1996.
Shigeo Nishimura et al., Chemistry Letters, pp. 963-966 (1977).
E.L. Ernest et al., Organic Synthesis, vol. 50, pp. 13-15 (1970).
Beilstein Handbook of Organic Chemistry, E III 6, p. 126 (1960).
S. Arctander, Perfume and Flavor Chemicals, Montclair, N.J. (1969), monograph No. 441.
H.C. Brown et al., J. Am. Chem. Soc., vol. 98, pp. 3383-3384 (1979).
T. Ohkuma et al., J. Am. Chem. Soc., vol. 117, pp. 10417-10418 (1995).

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