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Synthetic method for 4oxo-beta-ionone

A technology of ionone and synthesis method, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of long reaction steps and low yield, and achieves easy separation, high yield, and low cost effect

Active Publication Date: 2012-06-27
CHINA TOBACCO HUNAN INDAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the reaction step of this method is long, and total productive rate is lower

Method used

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  • Synthetic method for 4oxo-beta-ionone
  • Synthetic method for 4oxo-beta-ionone
  • Synthetic method for 4oxo-beta-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 10g β-ionone and 40mLDMSO in the 150mL three-necked bottle that has condensing tube, add 0.408g (corresponding to 0.43% of the amount of substance of β-ionone) under stirring condition) phosphomolybdic acid, 0.224g (corresponding to β-ionone -3.8% of the amount of ionone substance) Potassium tert-butoxide, at 105 DEG C, feed oxygen through a bubbler, react for 20h, GC-MS detects the reaction result, and the total ion diagram is shown in the attachment figure 1 , normalized integration, the conversion rate of raw material β-ionone is 98.6%, and the selectivity of product 4-oxo-β-ionone is 91.3%. The isolated 4-oxo-β-ionone is a light yellow crystal with a melting point of 50°C to 52°C. Through GC-MS analysis, its molecular ion peak is 206 (molecular ion peak M + , abundance 72%), 163 (M + -CH 3 CO, 100%), 149 (M + -C 2 h 5 CO, 20%), 135 (M + -C 4 h 7 O, 25%), 121 (M + -C 5 h 9 O, 47%); IR / v1663cm -1 ; 1 H-MNR (CD 3 Cl, 400MHz): 1.14(s, 6H, 2H 3 C-C(4)...

Embodiment 2

[0020] Repeat Example 1 according to the same steps as described, but the reaction temperature is set to 115 ° C. After the same reaction time, GC-MS detection, normalized integration, the conversion rate of raw material β-ionone is 100%, and the product 4-oxo The selectivity of substituted-β-ionone was 100%.

Embodiment 3

[0022] Repeat Example 1 according to the same steps as described, but the reaction temperature is set at 85°C. After the reaction for the same time, GC-MS detection, normalized integration, the conversion rate of raw material β-ionone is 70.36%, and the product 4-oxo The selectivity of substituted-β-ionone was 78.8%.

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Abstract

The invention relates to a synthetic method for 4-oxo-beta-ionone. The synthetic method comprises the following steps: using beta-ionone as materials, oxygen as oxidant, phosphomolybdic acid as catalyst, heating in organic solvent DMSO in the presence of potassium tert-butoxide for catalytic oxidation to obtain 4oxo-beta-ionone. In the method of the invention, 4oxo-beta-ionone can be synthesized after oxidation during one-step reaction, thereby overcoming the defect of complex steps in multi-step reaction. The invention also has the characteristics of high yield and high raw material conversion rate.

Description

technical field [0001] The invention relates to a method for synthesizing 4-oxo-β-ionone by using β-ionone as raw material. Background technique [0002] The structural formula of the raw material β-ionone used in the present invention and target product 4-oxo-β-ionone is as follows: [0003] [0004] β-ionone [0005] [0006] 4-oxo-β-ionone [0007] 4-Oxo-β-ionone is an important tobacco spice, which can play the role of delicate and soft cigarette smoke when added to cigarettes. At the same time, the carotenoid compounds synthesized by using it as an intermediate are applied in the fields of medicine and material science, and have received extensive attention in recent years. [0008] Oxyionone can be obtained from ionone through allylic oxidation. In the late 1940s, Oppenauer et al. synthesized 4-oxo-β-ionone by oxidation of tert-butyl chromate. The existing methods mainly include chromium salt oxidation, sodium chlorate oxidation, biological oxidation, electro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/647C07C45/34B01J27/19
Inventor 杨华武唐瑞仁黎艳玲朱卓越陈雄苏利霞赵瑜钟科军
Owner CHINA TOBACCO HUNAN INDAL CORP