Method for making keto acids and dione cyclics obtained therefro

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

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562499, 562577, 562508, 568346, 568377, C07C 51285

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043407536

ABSTRACT:
A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.

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Henshall et al., The Cyclization of 3,3 Dimethyl-5-keto-hexanoic Acid, J.A.C.S., 77, 6656, 1955.
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Eastman Organic Chemical Bulletin, vol. 48, No. 1, 1976.
5,5-Dimethyl-1,3-cyclohexanedione (1,3-Cyclohexanedione,5,5-dimethyl-), Shriner et al., Organic Synthesis., Coll. Vol., pp. 200-202.
Total Synthesis of Polycyclic Triterpenes: The Total Synthesis of (+) -Onocorin, Stork et al., J. Amer. Chem. Soc., 85, 3419 (1963).

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