Method for preparing 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecatriene

A technology of undecanetriene and dialkoxy, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of difficult synthesis, difficult sources, difficult industrial production, etc., and achieve low cost , The process route is simple and the raw materials are easy to obtain

Active Publication Date: 2012-01-11
启东欧常新材料有限公司
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Although this method has more industrialization potential, the raw material 4-methyl-5,5-dialkoxy-1-pentene-1-phosphonic acid dialkyl ester (10) used in it has difficult sources, and the synthesis difficulty is also Larger and more difficult to apply to industrial production; it is particularly worth mentioning that the C14 acetal (2) prepared by this method is a mixture of four cis-trans isomers

Method used

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  • Method for preparing 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecatriene
  • Method for preparing 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecatriene
  • Method for preparing 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecatriene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Preparation of (2E)-3,7-dimethyl-2,6-octadiene-1-triphenylphosphonium chloride (3A).

[0038] In a 1000mL four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer, add 90g of triphenylphosphine, 52g of geranyl chloride ((E)-1-chloro-3,7-dimethyl-2,6 -octadiene) and 600 ml of toluene, refluxed for 8 hours. Cool down, filter, and dry the solid at 60-70°C to obtain 117 g of a white solid, with a yield of 89.7%.

[0039] Product structure confirmation:

[0040]

[0041] 1 HNMR (400MHz, CDCl 3) δ (ppm): 1.383(d, J=3.6Hz, 3H, C-9H); 1.507(s, 3H, C-8H); 1.564(s, 3H, C-10H); 2.036(s, 4H, C-4H ,C-5H); 4.247(dd, J=15.6Hz, 7.6Hz, 2H, C-1H); 4.915-4.935(m, 1H, C-6H); 5.134-5.183(m, 1H, C -2H); 7.722-7.880(m, 15H, -(C 6 H* 5 ) 3 ).

[0042] 13 CNMR (100MHz, CDCl 3 ) δ(ppm):15.685, 15.713; 16.548; 22.346,22.848; 24.636; 25.439; 25.472; 39.182, 39.211; 108.302, 108.397; 118.118, 118.970; 123.455; 130.038, 130.274; 131.637; 133...

Embodiment 2

[0044] Example 2: Preparation of (3-E and 3-Z)-2,6,10-trimethyl-1,1-dimethoxy-3,5,9-undecanetriene (2A).

[0045] In a nitrogen-protected 500ml three-neck flask, add 43.5 g of (2E)-3,7-dimethyl-2,6-octadiene-1-triphenylphosphonium chloride (3A) (0.10 mol) and 100 Add 12.4 grams of potassium tert-butoxide (0.11 mol) in batches at -30 to -25°C under mechanical stirring for about half an hour. After the addition, continue to insulate and stir for about 1 hour to fully dissociate the carbanions. Then keep -30~-25℃ and add 13.2 grams of 2-methyl-3,3-dimethoxy-1-propanal (4A) (0.10 mol) dropwise, and the dropwise addition is completed in about 1 hour, and continue to keep stirring for about half After 1 hour, add 50 ml of water and 100 ml of diethyl ether and stir for 10 minutes, separate layers, evaporate the diethyl ether to dryness, add 100 ml of n-hexane and 100 ml of 1:1 methanol water (v:v) solution, stir for 10 minutes, then separate layers, n-hexane The alkane layer was wa...

Embodiment 3

[0052] Example 3: Preparation of tomato with (3-E and 3-Z)-2,6,10-trimethyl-1,1-dimethoxy-3,5,9-undecanetriene (2A) red pigment (1).

[0053] Under nitrogen protection, 12.6 grams of (3-E and 3-Z)-2,6,10-trimethyl-1,1-dimethoxy-3,5,9- Add undecanetriene (0.05mol), 100ml tetrahydrofuran and 1.2g p-toluenesulfonic acid into a 250ml four-neck flask, stir evenly, add 22g water dropwise, stir and react at 20-25°C for one day, and track the reaction by gas chromatography After the reaction was basically completed, a solution prepared by adding 2 grams of sodium bicarbonate and 20 milliliters of water was added for neutralization, and the tetrahydrofuran was distilled off under reduced pressure by a water pump, then 100 milliliters of cyclohexane was added, and the organic layer was separated after layering. The organic layer was washed with 30 ml of water, dried over anhydrous magnesium sulfate, and the solvent was recovered under reduced pressure to obtain 10.5 g of 2,6,10-trimeth...

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Abstract

The invention relates to a method for preparing 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecatriene, belonging to the technical field of lycopene intermediate synthesis methods. The method comprises the following steps: (1) under the protection of inert gas and in the presence of an organic solvent and alkali, carrying out dissociation reaction on C10 triphenyl phosphonium salt at the temperature of minus 40-30 DEG C; and (2) after the dissociation reaction in the step (1) is completed, adding C4 acetal, carrying out Wittig condensation reaction at the temperature of minus 40-30 DEG C in the presence of the organic solvent and alkali so as to obtain 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecatriene. The method provided by the invention has the advantages of concise process route and easy obtainment of raw materials, low cost and high industrial value.

Description

Technical field: [0001] The present invention relates to the synthesis of lycopene intermediates, specifically a kind of 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecanetriene (hereinafter referred to as C14 acetal) preparation method. Background technique: [0002] There are about 600 carotenoids in nature, but only six of them can be used in industrial production. The manufacturers are Roche and BASF. As one of the important products, lycopene plays an important role in scavenging free radicals, anti-aging, inhibiting tumors, and treating heart disease. It is widely used in drugs, food additives, and feed additives. Roche has developed a synthetic route characterized by the Wittig reaction using triphenylphosphine, and other early synthesis methods also used triphenylphosphine. [0003] In WO 0031086, Babler J. H. et al reported a new method for the synthesis of lycopene characterized by the Wittig-Horner reaction, using 3,7,11-trimethyl-2,4,6,10-tetra Diethyl dodecyl phosp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/303C07C41/48
Inventor 沈润溥吴春雷陶菲菲刘伟
Owner 启东欧常新材料有限公司
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