Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1968-05-01
1976-09-21
Schwartz, Gerald A.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2603461R, C07C 4912
Patent
active
039819205
ABSTRACT:
The invention provides a method for the preparation of 2-cyclopenten-1-one derivatives. The process involves metalating 2-methylfuran in the 5-position by an interchange reaction with an alkali metal-organic compound, condensing the resulting metal derivative of 2-methylfuran with a halide of the formula R--CH.sub.2 --X, wherein R represents an unsubstituted acyclic hydrocarbon radical which is free of triple bonds, comprises from 0 to 2 double bonds and contains from 3 to 5 carbon atoms and X represents a halogen, in order to form a 2,5-disubstituted furan of the formula ##EQU1## treating the disubstituted furan with an acidic agent to cause the opening of the furan ring and the formation of a dione of the formula ##EQU2## and cyclizing the dione by a treatment with alkali. The invention also provides certain novel 2-cyclopenten-1-one derivatives which are useful as fragrant ingredients in the manufacture of perfume compositions and which constitute valuable starting materials in the manufacture of other useful organic compounds.
REFERENCES:
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Beilstein's Handbuch der Organischen Chemie, vol. I, pp. 3161-3162 (1959).
Chemical Abstracts, vol. 50, 5569(b).
Gilman et al., J. Am. Chem. Soc. vol. 56, pp. 1123-27 (1934) *Gilman et al. III.
Morrison and Boyd, "Organic Chemistry" pp. 834, 837-838, and 840-841 (1959).
Gilman (I): Gilman et al., J. Am. Chem. Soc. vol. 61, 1939, pp. 109-112.
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Berichte (I): Berichte, vol. 75, pp. 447-454 (1942).
Berichte(II): Berichte, vol. 75, pp. 460-468 (1942).
Dunlop, The Furans, ACS Monograph Series 1953, pp. 640-642.
Firmenich S.A.
Schwartz Gerald A.
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