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Preparation method for jointly preparing beta-ionone

A technology for combined preparation of ionone and β-ionone, which is applied in the field of joint preparation of β-ionone, can solve the problems of cumbersome process and difficult operation, and achieve the effect of simple operation, high yield, and low requirements for raw materials and reaction environment

Inactive Publication Date: 2012-09-05
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 for jointly preparing beta-ionone
  • Preparation method for jointly preparing beta-ionone
  • Preparation method for jointly preparing beta-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of α-cyclic citral (VII)

[0031]

[0032] Dilute 45.6g (0.3mol) of citral with 45ml of dichloroethane and add it to a 250ml four-neck 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 complete...

Embodiment 2

[0037] Embodiment 2: the preparation of β-cyclic citral (VI)

[0038]

[0039]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. 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:

[0040] 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);

[0041] 1 HNMR (δ, ppm, 400MHz, CDCl 3 ): 1.19 (s, 6H, -CH 3 ), 1.43-1.46 (m, 2H, CH 2 -C), 1.60-1.66(m, ...

Embodiment 3

[0043] Embodiment 3: the mixture of α-cyclic citral (VII) and β-cyclic citral (VI) prepares β-ionone

[0044] In a 500ml four-necked bottle, add α-cyclocitral 15.4g, β-cyclocitral 15.0g (0.2mol in total) and 250g acetone, then add 5% sodium hydroxide aqueous solution 3ml, stir under the protection of nitrogen at 35- React at 45°C. 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 under normal pressure, and the oil pump vacuum distillation collected the 85-89°C / 1mmHg fraction to obtain 30.4g of the product (gas phase content 94.5%), and the yield was 74.8%. The first portion 9.4 grams is a mixture of α-cyclic citral, β-cyclic citral, α-ionone, and β-ionone (gas phase content 10.5%: 29.2%: 22.4%: 36.1%), which can be applied mechanically to the next batch reaction.

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Abstract

The invention discloses a preparation method for jointly preparing beta-ionone, relating to the technical field of organic intermediate synthesis. The method comprises the following steps: adding alpha-cyclocitral, beta-cyclocitral, acetone and sodium hydroxide water solution into a reaction bottle; mixing for reaction under the protection of nitrogen and tracing the reaction process by using gaschromatography; after the reaction is over, adding acids for neutralizing; after recycling the acetone at atmospheric pressure, vacuum distilling and collecting the distillations of 85-89 DEG C / 1mm Hg to obtain the product. The invention provides an entirely new method for preparing the beta-ionone. The invention uses the easy-preparing industry raw material alpha-cyclocitral to condense with theacetone and can directly prepare the beta-ionone, which changes the existing traditional thinking of methods for preparing the beta-ionone; the method has the advantages of simple and convenient operation, mild reaction conditions and high yield coefficient and has very important industrial value.

Description

technical field [0001] The invention relates to the synthesis of organic intermediates, in particular to a method for jointly preparing 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): C07C49/21C07C45/74C07C45/67
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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