Process for the production of 13-oxabicyclo(10.3.0)pentadecane a

Details Process for the production of 13-oxabicyclo(10.3.0)pentadecane a Process for the production of 13-oxabicyclo(10.3.0)pentadecane a

1985-01-10

1989-07-25

Jiles, Henry R.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549302, 558371, 558374, 562510, C07D30793, C07C30787

Patent

active

048515523

ABSTRACT:
13-oxabicyclo[10.3.0]pentadecane, a valuable ambergris fragrance, is prepared by reacting cyclododecanone with cyanoacetic acid in the presence of a Knoevenagel catalyst to form cyclododecenylacetonitrile, the nitrile is hydrolyzed to cyclododecenylacetic acid, and the acid is cyclized to the lactone, and the lactone is reduced to the corresponding diol which is cyclized to 13-oxabicyclo[10.3.0]pentadecane.

REFERENCES:
patent: 2007813 (1935-07-01), Scheuing et al.
patent: 4222904 (1980-09-01), Meins et al.
DiBiase et al., J. Org. Chem., vol. 44(25), pp. 4640-4649 (1979).
Fieser and Fieser, Advanced Org. Chem., Reinhold Publ., pp. 365-366 (1961).
Modern Synthetic Reactions, Herbert O. House, W. A. Benjamin, Inc. Menlo Park, California (1972) pp. 649-650.

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