Method for making bicyclic lactones

C - Chemistry – Metallurgy – 07 – D

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260/359.3

C07D 311/76 (2006.01) C07D 311/00 (2006.01) C07D 311/94 (2006.01) C07D 315/00 (2006.01)

Patent

CA 1308111

ABSTRACT A method for making a bicyclic lactone comprising heating under aqueous acidic conditions a beta, gamma unsaturated cyclic nitrile of the formula Image wherein R3, R4, R5, and R6 are independently selected from the group consisting of -H, -CH3; R2 is selected from the group consisting of -H, -CH3, and -C2H5: R8 is -H or -CH3; 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 m + o + p is an integer from 3 to 5; and an aldehyde having the formula Image wherein R1 is selected from the group consisting of -H and -CH3, for a length of time sufficient to convert at least a portion of the reactants to a bicyclic lactone of the formula Image wherein R1,R2, R4, R5, R6, m, o, and p are as defined above, R3 is -CH3, or if R8 is hydrogen, R3 together with R7 represents a carbon-carbon bond, R7 together with either R3 or R8 represents a carbon- carbon bond, and R8 is -H, or if R3 is -CH3, R8 together with R7 represents a carbon-carbon bond.

515973

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