Hydrogenation of cyclic unsaturated compounds

Details Hydrogenation of cyclic unsaturated compounds Hydrogenation of cyclic unsaturated compounds

1975-05-06

1977-11-15

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260617C, 260631H, C07C 2900, C07C 3508

Patent

active

040585727

ABSTRACT:
In a process for hydrogenation, with elemental hydrogen gas in the presence of a hydrogenation catalyst, of a cyclic unsaturated compound having an hydroxyl group projecting from an asymmetric center of the ring and an olefinic carbon-to-carbon double bond which when saturated in the hydrogenation process creates an additional asymmetric center in the ring, the improvement for obtaining increased stereoselectivity by increasing the addition of said hydrogen to that side of the olefin bond on the same side of the compound molecule as said hydroxyl group, comprising: conducting said hydrogenation with a nickel hydrogenation catalyst that has a substantial fraction of its reactive surfaces inactivated.
The invention is particularly applicable to the hydrogenation of d-trans-piperitol to d-isomenthol.

REFERENCES:
patent: 3028418 (1962-04-01), Webb
Pattison, et al., J.A.C.S., vol. 73, pp. 611-613, (1951).
Eliel, Stereochemistry of Carbon Compounds, pp. 434-446, (1962).
Smith, J.A.C.S., vol. 72, pp. 3454-3458, (1950).
Mitsui et al., Chem. & Ind., vol. 1967, pp. 1746-1747.
Tyman et al., Tetrahedron Letters, No. 20, pp. 1773-1775, (1973).

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