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Citation: HU Tie, PI Shaofeng, WANG Ye, GAO Haili, SUN Hanzhou, LI Jilie. Synthesis of Irone by Cyclization Reaction[J]. Chinese Journal of Applied Chemistry, ;2014, 31(11): 1297-1301. doi: 10.3724/SP.J.1095.2014.40024 shu

Synthesis of Irone by Cyclization Reaction

HU Tie ^a,b ,
PI Shaofeng ^a ,
WANG Ye ^a ,
GAO Haili ^a ,
SUN Hanzhou ^a,, ,
LI Jilie ^a,,

1.
a 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.
b Guangzhou Maritime Institute, Guangzhou 510725, China

Corresponding author: SUN Hanzhou, LI Jilie,
Received Date: 20 January 2014
Available Online: 28 March 2014
Fund Project: 国家林业局948项目(2011-4-17) (2011-4-17)

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.
- irone,
- cyclization reaction,
- cyclomethylene pseudoionones,
- selectivity of α-irone
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