Process for the preparation of macrocyclic ketones

Details Process for the preparation of macrocyclic ketones Process for the preparation of macrocyclic ketones

1974-11-04

1977-05-24

Morgenstern, Norman

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260586R, 260586M, 260617H, 260617M, 260648D, 260666A, C07C 4500, C07C 4516

Patent

active

040255620

ABSTRACT:
Saturated cyclic ketones having 12 to 20 carbon atoms in the ring, such as muscone, are prepared by (a) the reaction of a cyclic olefin with a dihalocarbene, (b) dehalogenation of the resulting dihalobicylic compound to form a cyclic allene, (c) hydration and oxidation of the cyclic allene to form an unsaturated cyclic ketone, and (d) conversion of the unsaturated cyclic ketone to a saturated cyclic ketone, with optional introduction of an alkyl substituent.

REFERENCES:
patent: 2526171 (1950-10-01), Stoll
patent: 3586720 (1971-06-01), Knepper et al.
Bach, "Tetra. Lett," No. 56, pp. 5841-5844 (1968) Pergamon Press.
Sharma et al., "J. Org. Chem.", 32, p. 241-244, (1967).
Muhlstadt et al., "Chem. Ber.," 100, pp. 223-227 (1967).
Mozacki et al., "Can. J. of Chem.," vol. 44, pp. 1021-1026 (1966).
Makosza et al., "Tetra. Letters", No. 53, pp. 4659-4662 (1969).
Freser et al., "Reagents For Org. Syn.", vol. 4, pp. 27-31 (1974).

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