Preparation of optically active allethrolone

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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C07C 4524

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041119940

ABSTRACT:
A process for the preparation of optically active allethrolone of (S) or (R) configuration comprising reacting in at least one organic solvent a sulfonate of optically active allethrolone of (R) or (S) configuration of the formula ##STR1## wherein X is selected from the group consisting of alkyl of 1 to 3 carbon atoms and phenyl optionally substituted in the p-position with a member of the group consisting of methyl, chlorine, bromine and fluorine with a salt of an organic carboxylic acid selected from the group consisting of aliphatic carboxylic acids of 1 to 6 carbon atoms optionally substituted with one or more halogens and a monocyclic aromatic carboxylic acid to form the ester of the carboxylic acid and (S) or (R) allethrolone antipodal to that of the starting sulfonate of allethrolone and subjecting the latter to acid hydrolysis to form (S) or (R) allethrolone antipodal to the starting sulfonate which allethrolones form insecticidally active esters with cyclopropane carboxylic acids.

REFERENCES:
patent: 2891888 (1959-06-01), Guest et al.
patent: 3720703 (1973-03-01), Elliot et al.
patent: 4005146 (1977-01-01), Goffmet
La Forge et al., "J. Org. Chem," 19,457 (1954).
La Forge et al., "J.A.C.S." 74 (1952) p. 5392.

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