1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone and fragran

Perfume compositions – Perfume compositions – Ring containing active ingredient

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568374, 568819, 568361, A61K 746

Patent

active

051643650

ABSTRACT:
The present invention concerns the novel odorant 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, I, a process for the manufacture of I, novel intermediates used in the process and fragrance compositions containing I. ##STR1## The process for the manufacture of 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone comprises hydroborating 1,1,2,3,3,6-hexamethyl-4,7-dihydroindane and oxidizing the hydroboration product to 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, or reductively alkylating, especially methylating, 5-nitro-1,1,2,3,3,6-hexamethylindane and converting the resulting 5-dialkyl-amino-1,1,2,3,3,6-hexamethylindane into 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone by reduction of the benzene ring and hydrolysis of the resulting enamine.

REFERENCES:
patent: 3773836 (1973-11-01), Hall
patent: 3847993 (1973-11-01), Hall et al.
patent: 3927083 (1975-12-01), Hall et al.
H. Brown, "Hydroboration", W.A. Benjamin Inc., N.Y. 1962 pp. vii-xiii.
D. G. Lee, "Oxidation", R. L. Augustine, editor, Marcel Dekker Inc., N.Y. 1969 pp. 56-81.
R. G. Curtis et al., J. Chem. Soc. (1953) 457.
Org. Syn. Coll. vol. 5, J. Wiley & Sons, N.Y. (1973) 552.
Houben-Weyl, "Methoden der Organischen Chemic" vol. V,Ib (1972) 613.

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