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Method for synthesizing oxo-alpha-ionone or oxo-beta-ionone

A technology of ionone and oxo, which is applied in the field of oxo α or β-ionone, can solve the problems of less than 40% yield, unsatisfactory yield, lengthy synthesis process, etc., and achieves shortened reaction time and cost. Low, the effect of improving the reaction efficiency

Active Publication Date: 2010-08-18
CHINA TOBACCO HUNAN INDAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the yields obtained by these synthetic methods are unsatisfactory, or the synthetic process is tedious, and the process is complicated; or use some precious metals and its complexes; or use unfriendly reagents to the environment, such as chromium trioxide, Chromium trioxide-pyridine, tert-butyl chromate, pyridinium dichromate, pyridinium chlorochromate, etc.
And in the patent US:4209450 [P] that people such as HagenJaedicke report, it is made solvent with chloroform, and what its oxidizing agent used is the oxidizing agent pair that sodium chlorate and potassium iodide are formed, and the reaction time reaches 24 hours, and productive rate is less than 40%, and Post-processing is more complex

Method used

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  • Method for synthesizing oxo-alpha-ionone or oxo-beta-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: Synthesis of 4-oxo-β-ionone

[0017] 19.2g of β-ionone, 13.5g of sodium bromate, 40g of 7% sulfuric acid solution, and 60ml of tetrahydrofuran were reacted at a controlled temperature of about 45°C. After 2.0 hours, samples were taken for GC-MS detection. The conversion of raw materials was basically complete, and the reaction was stopped. The GC-MS detection results showed that the chromatographic peak area ratio of 4-oxo-β-ionone was 91.7%, and the chromatographic peak area ratio of 5,6-epoxy-β-ionone was 7.5%. Separate the liquid, wash with water, remove the salt solution, extract the aqueous solution with 2*20ml of ether, combine the organic phases, rotary evaporate, and evaporate the solvent to dryness to obtain (yield: 67%) 4-oxo-β-ionone.

[0018] The isolated 4-oxo-β-ionone is a colorless 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...

Embodiment 2

[0020] Embodiment 2: Synthesis of 4-oxo-β-ionone

[0021] 19.2g of β-ionone, 13.5g of sodium bromate, 40g of 12% sulfuric acid solution, and 60ml of tetrahydrofuran were reacted at a controlled temperature of about 45°C. After 1.5 hours, samples were taken for GC-MS detection. The conversion of raw materials was basically complete, and the reaction was stopped. The GC-MS detection results showed that the chromatographic peak area ratio of 4-oxo-β-ionone was 84.5%. 4-Oxo-β-ionone was obtained (yield: 58%).

[0022] Subsequent reaction is the same as in Example 1, below.

Embodiment 3

[0023] Embodiment 3: Synthesis of 4-oxo-β-ionone

[0024] β-ionone 19.2g, sodium bromate 13.5g, 7% sulfuric acid solution 40g, 60ml acetone, control the temperature to react at about 45°C, take a sample after 2.0h for detection by GC-MS, 4-oxo-β-ionone The peak area of ​​the chromatographic peak reaches 78%. 4-Oxo-β-ionone was obtained (yield: 47%).

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Abstract

The invention belongs to the technical field of fine chemical industry, and discloses a method for synthesizing oxo-alpha-ionone or oxo-beta-ionone. The method is realized in a way that: adopting alpha-ionone or beta-ionone to react with sodium bromate in the mixed solvent of acid solution and hydrophilic organic solvent at the temperature of lower than 80 DEG C for 0.5-12 hours, thereby synthesizing the oxo-alpha-ionone or oxo-beta-ionone in one step. The invention has the advantages of simple operation, short reaction time, mild conditions, environment friendliness and high yield. The obtained oxo-alpha-ionone or oxo-beta-ionone has the advantage of high purity, can be widely used in food addiitives, cosmetics, medicines, cigarets and the like, and has high application value.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a method for preparing corresponding oxo-alpha or beta-ionone from alpha or beta-ionone. Background technique [0002] Oxo-α or β-ionones include 4-oxo-β-ionone (I) and 3-oxo-α-ionone (II), which are very important tobacco flavors and organic synthesis intermediates , commonly used in the preparation of essence and preparation of heterocyclic compounds and synthetic intermediates of mastigtrienone in tobacco flavors, etc. [0003] [0004] 4-Oxo-β-ionone is a good flavor for tobacco. It can be added to cigarettes to play a delicate and soft cigarette smoke effect. At the same time, carotenoid compounds synthesized with it as an intermediate It has been widely concerned in the fields of medicine and material science in recent years. 3-Oxo-α-ionone is mainly used in food, cosmetics and fragrance industries, and it is also a key intermediate for the synthesis of carotenoid...

Claims

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Application Information

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IPC IPC(8): C07C49/647C07C45/30
Inventor 朱卓越杨华武赵瑜陈雄黎艳玲苏利霞钟科军谭新良
Owner CHINA TOBACCO HUNAN INDAL CORP
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