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Synthesis method of 4-oxo-beta-ionone

A technology of ionone and synthesis method, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of difficult recovery, pollute the environment, low yield and the like, achieve convenient post-processing and protect the environment , synthesizing simple effects

Inactive Publication Date: 2019-05-07
张宇
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Problems solved by technology

Among them, the disadvantages of the chromium salt oxidation method are pollution of the environment; the conditions of the sodium chlorate oxidation method are not easy to control; the biological oxidation method is difficult to realize industrial production; the electrolytic oxidation method has many by-products, the yield is low, and the energy consumption is large; the molecular oxygen oxidation method is not easy to select a catalyst , it is difficult to achieve industrialization
[0003] Tan Xinliang et al. reported that NHPI and Co(AcAc)2 were used as catalysts to directly oxidize β-ionone to obtain products with a yield as high as 70%. However, the amount of catalyst NHPI is large, difficult to recycle, high cost, and large pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] A kind of synthetic method of 4-oxo-beta-ionone, this synthetic method comprises the steps:

[0016] Add 100g of β-ionone, 9g of N,N,N-trihydroxyisocyanuric acid (THICA) and 1.4g of copper acetylacetonate Cu(AcAc) in a 250mL four-neck flask in sequence, stir mechanically, and pass oxygen through the reaction flask , heated in a water bath at 60°C;

[0017] Use gas chromatography to track and detect the reaction solution until all the reactants are converted, filter, wash with 50ml of absolute ethanol three times to obtain a yellow solid, recover the mother liquor, and distill the mother liquor under reduced pressure to remove the solvent to obtain a light yellow solid crude product, namely 4-oxo-β - 95.2 g of ionone, recrystallized with v (ethyl acetate): v (petroleum ether) = 2: 8 to obtain 83.8 g of pure 4-oxo-β-ionone, with a yield of 78.2%.

[0018] 1HNMR (400MHz, CDCl3), δ / 10 －6 : 1.93( s, 6H, 2CH3) ; 1.804( d, J = 0.4Hz, 3H, C = CCH3) ; 1.896( t, J = 7.2Hz, 2H, ...

Embodiment 2

[0020] A kind of synthetic method of 4-oxo-beta-ionone, this synthetic method comprises the steps:

[0021] Add 105g of β-ionone, 10g of N,N,N-trihydroxyisocyanuric acid (THICA) and 1.5g of copper acetylacetonate Cu(AcAc) to a 250mL four-necked flask in sequence, stir mechanically, and pass oxygen through the reaction flask , heated in a water bath at 60°C;

[0022] Use gas chromatography to track and detect the reaction solution until all the reactants are converted, filter, wash with 50ml of absolute ethanol three times to obtain a yellow solid, recover the mother liquor, and distill the mother liquor under reduced pressure to remove the solvent to obtain a light yellow solid crude product, namely 4-oxo-β - 96.1 g of ionone was recrystallized with v (ethyl acetate): v (petroleum ether) = 2: 8 to obtain 84.8 g of pure 4-oxo-β-ionone, with a yield of 79.0%.

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Abstract

The invention belongs to the field of organic matter synthesis, and particularly relates to a synthesis method of 4-oxo-beta-ionone, wherein beta-ionone is subjected to molecular oxygen oxidation by using N,N,N-trihydroxyisocyanuric acid (THICA) and cupric acetylacetonate (AcAc) 2 as catalysts so as to prepare the 4-oxo-beta-ionone in one-step reaction. According to the present invention, the synthesis method is used so as to achieve advantages of cost reducing, environment protection, simple operation, convenient post-treatment, high yield and simple synthesis, and is suitable for industrialproduction.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a synthesis method of 4-oxo-β-ionone. Background technique [0002] 4-Oxo-β-ionone is an important synthetic fragrance, which can improve the quality of cigarette smoke, and has a significant flavoring effect while reducing smoke tar and nicotine. At the same time, 4-oxo-β-ionone is also an important intermediate in the synthesis of carotenoids. There are many reports related to the synthesis of 4-oxo-β-ionone, mainly including chromium salt oxidation, sodium chlorate oxidation, biological oxidation, electrolytic oxidation, and molecular oxygen oxidation. Among them, the disadvantages of the chromium salt oxidation method are pollution of the environment; the conditions of the sodium chlorate oxidation method are not easy to control; the biological oxidation method is difficult to realize industrial production; the electrolytic oxidation method has many by-p...

Claims

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Application Information

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IPC IPC(8): C07C45/34C07C49/647
Inventor 张宇
Owner 张宇
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