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Preparation method of beta-ionone

A technology of ionone and acetone, which is applied in the field of preparation of beta-ionone, can solve the problems of cumbersome process and difficult operation, and achieves the effects of simple operation, high yield and mild conditions

Inactive Publication Date: 2012-08-22
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] There is a disadvantage in the above methods: that is, the process is cumbersome and the operation is difficult.

Method used

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  • Preparation method of beta-ionone
  • Preparation method of beta-ionone
  • Preparation method of beta-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of α-cyclic citral (VII)

[0030]

[0031] Dilute 45.6g (0.3mol) of citral with 45ml of dichloroethane and add it to a 250ml four-necked flask, keep warm in a water bath, and slowly drop into a solution of 30.0g of aniline in 30ml of dichloroethane while stirring at room temperature. After the dropwise addition was completed, the mixture was stirred for another half an hour, and the TLC reaction was completed (developing solvent: ethyl acetate:petroleum ether=1:3). The reaction mixture was dried with 8 g of anhydrous sodium sulfate, and the dried dichloroethane solution of citralimine could be directly used in the cyclization reaction. Add 120ml of 98% concentrated sulfuric acid and 140ml of dichloroethane into a 500ml four-necked bottle, mix and stir, cool in a cold bath to -20~-25°C, and slowly drop the imine solution prepared above into it under vigorous stirring. The temperature was controlled at about -20°C, the addition was comple...

Embodiment 2

[0036] Embodiment 2: Condensation reaction prepares β-ionone

[0037]In a 500ml four-necked flask, add 30.4g (0.2mol) of α-cyclocitral and 250g of acetone, then add 3ml of 5% aqueous sodium hydroxide solution, and stir the reaction at 35-45°C under nitrogen protection. After about 6 hours, the gas chromatography tracked that the raw material basically disappeared, and 1ml of acetic acid was added, and the acetone was recovered at normal pressure. After the acetone was recovered under normal pressure, the 85-89 ° C / 1mmHg fraction was collected by oil pump vacuum distillation to obtain 29.4 g of the product (93.5% in gas phase content), and the yield was 71.6%. The first portion 10.2 grams is a mixture of α-cyclic citral, β-cyclic citral, α-ionone, and β-ionone (gas phase content 15.5%: 29.5%: 26.3%: 29.1%), which can be applied mechanically to the next batch reaction. Product structure verification:

[0038] GC-MS (m / e): 192, 177 (100%), 162, 149, 135, 121, 107, 91, 77, 43; I...

Embodiment 3

[0041] Embodiment 3: the preparation of β-cyclic citral (VI)

[0042]

[0043] Dilute 0.3g KOH with 60ml of methanol and add it into a 250ml three-neck flask, and add 30.4g (0.2mol) of α-cyclocitral dropwise under stirring at room temperature. After the dropwise addition was completed, the stirring was continued for about 1 hour, and the reaction was followed by gas chromatography, and then 1.2 g of concentrated hydrochloric acid was added to terminate the reaction. The solvent was recovered, the residue was distilled under reduced pressure, and 25.5 g of 60-65°C / 1mmHg fraction was collected as a colorless transparent liquid with a gas phase content of 98.5% and a yield of 83.9%. Product structure verification:

[0044] GC-MS (m / e): 152, 137 (100%), 123, 109, 95, 91, 81, 67, 55, 43, 41; IR (v / cm -1 ): 1672 (-CHO, characteristic peak of aldehydes), 1612 (double bond);

[0045] 1 HNMR (δ, ppm, 400MHz, CDCl 3 ): 1.19 (s, 6H, -CH 3 ), 1.43-1.46 (m, 2H, CH 2 -C), 1.60-1.6...

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Abstract

The invention discloses a preparation method of beta-ionone, which belongs to the technical field of synthesis of organic intermediates and comprises the following steps of: adding alpha-cyclocitral and acetone as well as a sodium hydroxide water solution into a reaction bulb; stirring for reaction under the protection of nitrogen, tracking the reaction process by gas chromatogram; when the reaction is ended, adding acid for neutralization; and after recycling the acetone under normal pressure, decompressing and rectifying for collecting 85-89DEG C / 1mmHg fractions to obtain the product. The invention provides a novel preparation method of the beta-ionone. The invention can directly prepare the beta-ionone by condensing the simply and easily prepared alpha-cyclocitral as an industrial raw material with the acetone, which changes the traditional design of the traditional preparation method of the beta-ionone. Meanwhile, the invention has the advantages of simple and convenient operation, mild condition, high yield and very important industrialized value and the like.

Description

technical field [0001] The present invention relates to the synthesis of organic intermediates, in particular to a preparation method of β-ionone. Background technique [0002] β-ionone (I) is an important intermediate in organic synthesis, as an important intermediate in the synthesis of vitamin A and carotenoids, and also an important spice (Editorial Committee of Chemical Encyclopedia. Chemical Encyclopedia [M]. Beijing: Chemical Industry Press, 1997 first edition, Vol.16:719-729). Its main synthetic route is: Method A. Use citral (II) as raw material, and acetone in the presence of alkaline reagents, synthesize intermediate pseudoionone (III) through condensation reaction; then under acidic conditions, through ring closure reaction Obtain β-ionone, which was obtained by Tiemann in 1893 (edited by E.T. Seymer, translated by Chen Zufu, Fragrance and Fragrance Chemistry [M], Science Press, first edition in 1989, 192-200) . The synthesis reaction is as follows: [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/21C07C45/74
Inventor 沈润溥吴春雷张符陶菲菲王林霞范少楼吴毅斌党松年
Owner SHAOXING UNIVERSITY
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