Method for producing optically active α-ionone

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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C560S128000, C560S225000, C560S227000, C560S228000, C560S231000

Reexamination Certificate

active

08053592

ABSTRACT:
Provided that a method for inexpensively producing optically active α-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active α-ionone obtained by the aforementioned method. A method for producing optically active α-ionone, comprising allowing α-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained α-ionone enol ester; a method for producing optically active α-ionone comprising subjecting α-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active α-ionol to react with an esterification agent to give an optically active α-ionol ester, hydrolyzing the obtained optically active α-ionol ester after purification as necessary, and then oxidizing the obtained optically active α-ionol; and a perfume composition comprising thus obtained optically active α-ionone.

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Oritani, T. et al., “Synthesis and absolute stereochemistry of chiral-ionone and dihydro-ionone” (1987), Agric. Biol. Chem,. vol. 51, No. 5, p. 1271-1275.
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Bovolenta et al. “A Simple and Efficient Highly Enantioselective Synthesis of Alpha-Ionone and Alpha-Damascone,” Journal of Organic Chemistry, vol. 69, pp. 8959-8962 (2004).
Fuganti et al., “Synthesis and Olfactory Evaluation of (+)- and (−)-γ-Ionone,” Helvetica Chimica Acta, vol. 83, pp. 2761-2768, 2000.

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