Novel bicyclic scents

Details Novel bicyclic scents Novel bicyclic scents

1978-08-28

1980-09-23

Brust, Joseph Paul

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

Organic compounds

Oxygen containing

260464, 560120, 568820, 585 21, 585357, 252522R, C07C 3305, C07C 4734, C07C12148, C07C 6974

Patent

active

042242533

ABSTRACT:
Novel 2-methylene-3-methyl-3-(1',3'-pentadien-1'-yl)-bicyclo-[2,2,1]-heptanes substituted in the 4'-position by methyl, alkoxycarbonyl, formyl, hydroxymethyl or cyano are obtained by reacting the novel aldehyde 2-methylene-3-methyl-3-formyl-bicyclo-[2,2,1]-heptane with 3-methyl-, 3-alkoxycarbonyl- or acetalized 3-formyl-2-butene-1-triarylphosphorylidene under the conditions of a Wittig reaction, with or without hydrolytic cleavage of the acetal group, or hydrolytic cleavage of the acetal group followed by reduction of the formyl group to the hydroxymethyl group, or hydrolytic cleavage of the acetal group, reaction of the aldehyde with a hydroxylammonium salt, and dehydration of the resulting oxime.
The novel compounds are distinguished by interesting scent characteristics.

REFERENCES:
patent: 3662007 (1972-05-01), Fanta et al.
patent: 3662008 (1972-05-01), Kretschmar et al.
patent: 3673256 (1972-06-01), Pieper et al.
patent: 3673261 (1972-06-01), Kretschmar et al.
patent: 4010213 (1977-03-01), Naegeli
patent: 4128509 (1978-12-01), Schleppnik
Kretschmar, et al., Tetrahedron Letters, 1970, pp. 41-44.
Christenson, et al., J. Org. Chem., 44, 1979, pp. 2012-2018.
Demole et al., Helv. Chim. Acta, 59 (1976), pp. 737-747.
Trippett, Quarterly Reviews, 17 (1963), pp. 406-440.
Buddrus, Angew. Chem., 80 (1978), pp. 535-536.
Brieger, Tetrahedron Letters, 28 (1963), pp. 1949-1951.

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