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A kind of method for efficiently preparing oxyionone

A technology for ionone and ionone molar amount is applied in the field of efficient preparation of oxoionone, which can solve the problems of low reaction yield and the like, and achieve the effects of environmental friendliness and low cost

Active Publication Date: 2022-05-10
CHINA TOBACCO ANHUI IND CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction of active manganese dioxide catalyzed oxidation of allylic sites has also been reported (such as Progress in Fine Petrochemical Industry, 2007, 8(9), 46-48; Journal of Advanced Chemical Engineering, 2000, 14(5), 448-452; Chemical World, 2000(Z1), 20-21; Zhejiang Chemical Industry, 1999, 30(2), 31-33; Fine Chemical Industry, 1997, 14(4), 45-46, etc.), but the substrates of these reactions are all benzyl Oxidation of hydrogen, has great limitations, and the reaction yield is low

Method used

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  • A kind of method for efficiently preparing oxyionone
  • A kind of method for efficiently preparing oxyionone
  • A kind of method for efficiently preparing oxyionone

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Embodiment Construction

[0019] The general operation steps are as follows: add 0.1mol ionone, 20mL solvent, and an appropriate amount of manganese dioxide in a three-necked flask with a condenser, stir and react for a certain period of time at an appropriate temperature, stop the reaction, and separate by column chromatography (petroleum ether) / ethyl acetate=6 / 1, v / v) to obtain the target product.

[0020] Example parameters are shown in the table below:

[0021]

[0022]

[0023] 1) self-made manganese dioxide;

[0024] 2) 3-oxo-α-ionone (1), 1 H-NMR (CDCl 3 ,400MHz) δ: 6.83(m,1H),6.13(m,1H),5.80(m,1H),2.56(m,1H),2.41(m,2H),2.25(s,3H),2.09(s ,3H),0.98(s,6H);

[0025] 4-oxo-β-ionone (2), 1 H-NMR(CDCl3,400MHz)δ7.40(m,1H),6.33(m,1H),3.16(m,2H),2.34(s,3H),1.97(s,3H),1.32(m,2H ),1.24(s,6H);

[0026] 3) Isolated yield.

[0027] As can be seen from the table, when the solvent is DMF, the reaction temperature is 120°C, the reaction time is 4 hours, the catalyst is gamma manganese dioxide, and...

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Abstract

The invention discloses a method for efficiently preparing oxyionone, which uses manganese dioxide as a catalyst to catalyze oxidation at the allyl position of ionone to obtain oxyionone. The method of the invention can synthesize oxyionone with a high yield, and has the advantages of simple operation, low cost and environmental protection.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a method for efficiently preparing oxyionone. Background technique [0002] Ionone has three isomers of α, β, and γ, and the structural formula is as follows: [0003] [0004] In natural products, there is mostly a mixture of α and β ionone, and no γ-ionone exists. In terms of taste, both α and β ionones have a strong sweet woody taste with a fruity sensory, slightly bitter, and a floral and woody aroma at the end. In comparison, α-ionone has a more sweet aroma, and β-ionone has more creamy and fruity aromas. Ionone can be used in a small amount in the essence of wine and tobacco flavor, and the ionone with lower purity can be used in soap. β-ionone can also be used as an intermediate of vitamin A. Derivatives of ionone is a carotenoid C widely present in various flowers, plants and tobacco. 13 Degradation products. In 1972, E.Demole et al. discovered an important componen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/647C07C45/28
CPCC07C45/28C07C2601/16C07C49/647
Inventor 徐志强徐迎波田振峰
Owner CHINA TOBACCO ANHUI IND CO LTD
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