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Citation: LIU Chang-Hui, LEI Cun-Xi, LONG Li-Ping, XIANG Ji-Guo. Improvement on Synthesis of 4-Oxo-β-ionone[J]. Chinese Journal of Applied Chemistry, ;2009, 26(5): 511-514. shu

Improvement on Synthesis of 4-Oxo-β-ionone

1.
Department of Chemistry and Environmental Engineering, Hunan City University, Yiyang 413000

Corresponding author: LEI Cun-Xi,
Received Date: 11 April 2008
Available Online: 16 June 2008
Fund Project: 湖南城市学院科研资助项目(07C002) (07C002)

The synthetic method of 4-oxo-β-ionone from α-ionone reported by Kaiser was improved.Factors that influnences epoxidation,ring opening and oxidation were discussed,and the purification method for title compound was investigated.Epoxidation of α-ionone with 30% H₂O₂ catalyzed by tungstophosphoric acid,4,5-epoxy-α-ionone was obtained with a yield of 85% and a purity of 94% when the mole ratio of α-ionone to H₂O₂ was 2:3 and that of tungstophosphoric acid to H₂O₂ was 5:100.Then it was converted into 4-hydroxyl-β-ionone under alkaline condition with a yield of 94% and a purity of 85% when the mole ratio of sodium methoxide to ionone epoxidation was 1.5:1.After purification of 4-hydroxyl-β-ionone by succine anhydride,the yield was 83% and the purity was 96%.After oxidation by aluminum isopropoxide,the yield was 93% and the purity was 96%.The title compound was obtained by column chromatography with a total yield of 61.7% compared with a yield of 47.2% obtained by Kaiser method.The structure of the compound was characterized by MS,IR,¹H NMR,¹³C NMR and elemental analysis.
- α-ionone,
- tungstophosphoric acid,
- aluminum isopropoxid,
- oxo-β-ionone
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