Method for making bicycle lactones from beta, gamma unsaturated

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549283, 549311, 549302, C07D31176

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active

047727284

ABSTRACT:
A method for making a bicyclic lactone comprising heating under aqueous acidic conditions a beta, gamma unsaturated cyclic nitrile and an aldehyde, for a length of time sufficient to convert at least a portion of the reactants to a bicyclic lactone of the formula ##STR1## wherein R.sub.3 is --H; R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of --H, --CH.sub.3 ; R.sub.2 is selected from the group consisting of --H, --CH.sub.3, and --CH.sub.3, and --C.sub.2 H.sub.5 ; R.sub.8 is --H or --CH.sub.3 ; m is an integer from 1 to 5; o is 0, 1, 2, or 3; and p is 0, 1, or 2; provided that the sum of m+o+p is an integer from 3 to 5; either R.sub.3 or R.sub.8 together with R.sub.7 represents a carbon-carbon bond. The method uses commercially available and relatively inexpensive raw materials as reactants.

REFERENCES:
patent: 3480634 (1969-11-01), Finkelstein et al.
patent: 3936473 (1976-02-01), Symon et al.
patent: 4219449 (1980-08-01), Lenselink et al.
Korte et al., Tetrahedron 1959, vol. 6, pp. 201-216.

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