Synthesis of Irone by Cyclization Reaction

doi:10.3724/SP.J.1095.2014.40024

Chinese Journal of Applied Chemistry

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Synthesis of Irone by Cyclization Reaction

HU Tie^1,2, PI Shaofeng¹, WANG Ye¹, GAO Haili¹, SUN Hanzhou^1*, LI Jilie^1*

(1.Key Laboratory of Cultivation and Protection for Non-Wood Forest Trees,Ministry of Education,
Central South University of Forestry and Technology,Changsha 410004,China；
2.Guangzhou Maritime Institute,Guangzhou 510725,China)

Received:2014-01-20 Revised:2014-03-25 Published:2014-10-09 Online:2014-10-09
About author:HU Tie，assistant; Tel：020-32082315; E-mail：121160342@qq.com; Research interests: Forest chemical engineering

Abstract

Abstract: The synthesis of irone was investigated by cyclization reaction from raw material 9,10-cyclomethylene pseudoionones. The cyclization mechanism was preliminarily studied. The optimal cyclization conditions for irone are to keep the reaction time within 45 min, the reaction temperature at -70 ℃, and the molar ratio of 9,10-cyclomethylene pseudoionones to chlorosulfonic acid at 1∶4. The combined yield of irone isomers can reach 90.1%, and the content of α-irone, β-irone and γ-irone are 60.2%, 29.0% and 8.0%, respectively, under the optimal cyclization conditions(determined by GC with area normalization method). The structures of irone isomers were also confirmed by 1H NMR and 13C NMR. Preliminary mechanism study indicates that the cyclization reaction for the synthesis of irone can finish rapidly at low temperature.

Key words: irone, cyclization reaction, cyclomethylene pseudoionones, selectivity of &, alpha, -irone

CLC Number:

O622.4

HU Tie1,2, PI Shaofeng1, WANG Ye1, GAO Haili1, SUN Hanzhou1*, LI Jilie1*. Synthesis of Irone by Cyclization Reaction[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.40024.

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Synthesis of Irone by Cyclization Reaction

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