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C15phosphonate ester compound, preparation method application thereof

A carbon pentadecanephosphonate and compound technology, applied in the field of 3-methyl-5--2, canthaxanthin synthesis, can solve the problems of low reaction yield, strong corrosiveness, difficult preparation and the like, and achieves the reaction yield. High rate, low cost, and the effect of industrialization

Inactive Publication Date: 2007-12-05
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Dialkyl chlorophosphite is used in this route, which is highly corrosive and difficult to prepare. It decomposes with water to produce acid mist, and the final condensation reaction yield is low, only 52%. The whole route is difficult to industrialize

Method used

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  • C15phosphonate ester compound, preparation method application thereof
  • C15phosphonate ester compound, preparation method application thereof
  • C15phosphonate ester compound, preparation method application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of 2-methyl-4-(2,6,6-trimethyl-3-hydroxycyclohexen-1-yl)-2-butenal

[0023] Mix 40g of 4-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-3-buten-2-one with 40g of methyl chloroacetate and cool to below -10°C , the temperature was controlled below -10°C, and 250 g of 30% sodium methoxide in methanol was added dropwise. Add 100mL of water, neutralize with acetic acid to neutrality, then add 200mL of ethyl acetate, separate the layers, then wash the layers with 100mL saturated aqueous sodium chloride solution, and wash the layers with 100 mL of saturated sodium chloride solution. Dry over magnesium sulfate, filter, and evaporate the solvent under reduced pressure to obtain 35 g of 2-methyl-4-(2,6,6-trimethyl-3-hydroxycyclohexen-1-yl)-2-butenal , yield 82%, GC content 91%. Boiling point: 105-108°C (2mmHg). 1 HNMR (400Hz, CDCl3): 0.990(s, 3H, CH3), 1.042(s, 3H, CH3), 1.681(s, 6H, CH3), 1.816(s, 4H, CH2 CH2), 2.180(s, 1H, OH), 3.051~3.064(d, 2H, CH2), 3...

Embodiment 2

[0024] Example 2: Synthesis of 3-methyl-5-(2,6,6-trimethyl-3-hydroxycyclohexen-1-yl)-1,3-pentadienephosphonic acid diethyl ester

[0025] Weigh 6.5g of 60% sodium hydride, wash with n-hexane, add 150mL of anhydrous toluene, add dropwise a solution of 50g of diethyl methylene bisphosphonate in 20mL of anhydrous toluene under nitrogen protection, and control the temperature at 25°C Next, after the dropwise addition was completed and then reacted for half an hour, 35g of 2-methyl-4-(2,6,6-trimethyl-3-hydroxycyclohexen-1-yl)-2-butenal was dissolved in 50mL The solution of anhydrous toluene was added dropwise at a temperature below 25°C. After the dropwise addition, the reaction was continued for one hour. After the reaction was completed, 200 mL of water was added to wash and separate the layers. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain 3-formazol 49 g of diethyl-5-(2,6,6-trimethyl-3-hyd...

Embodiment 3

[0027] Example 3: Synthesis of 3-methyl-5-(2,6,6-trimethyl-3-hydroxycyclohexen-1-yl)-2,4-pentadienephosphonic acid diethyl ester

[0028]Weigh 4.0 g of potassium tert-butoxide, dissolve it in 150 mL of anhydrous DMSO solution, add 3-methyl-5-(2,6,6-trimethyl-3-hydroxycyclohexene-1- Diethyl)-1,3-pentadienephosphonic acid diethyl ester 49g, control temperature 15-25 ℃, react for 2 hours after completion of dropwise addition, adjust pH to neutral with 10% aqueous acetic acid solution after reaction, add 200mL water and 200mL ethyl acetate, layered, the organic layer was washed once with 200mL water, layered, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain 3-methyl-5-(2,6,6-tri 46.6 g of diethyl methyl-3-hydroxycyclohexen-1-yl)-2,4-pentadienephosphonate as a viscous oil. Yield 95%. 1 HNMR (400Hz, DMSO): 0.857(s, 3H, CH3), 1.002(s, 3H, CH3), 1.252~1.330(6H, CH3), 1.260~1.362(m, 2H, CH2), 1.524~1.646(m, 2H, CH2) 1....

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Abstract

The present invention relates to C15 phosphonate compound for synthesizing canthaxanthin and its preparation process. The C15 phosphonate compound is made to react with 2, 7-dimethyl-2, 4, 6-octyltriene-1, 8-dialdehyde under the action of alkali to obtain 4, 4'-dihydroxy-beta-carotene; and 4, 4'-dihydroxy-beta-carotene is then oxidized with manganese dioxideor aluminum isopropoxide to obtain canthaxanthin. The new synthesis path is superior to available industrial canthaxanthin synthesizing process, and has simple technological process, high yield, low cost and no use of triphenyl phosphine and chlorinated dialkyl phosphite.

Description

technical field [0001] The present invention relates to chemical intermediates, specifically a kind of 3-methyl-5-(2,6,6-trimethyl-3-hydroxycyclohexen-1-yl)-2,4-pentadiene Dialkyl phosphonates, processes for their preparation and their use in the synthesis of canthaxanthin. Background technique [0002] The industrial synthesis of canthaxanthin is mainly obtained by oxidation of β-carotene as a raw material, with a general yield of 40-65%, high cost and many impurities. There are not many routes for the total synthesis of canthaxanthin. The literature Michael Rosenberger, Patrick McDougal, Julie Bahr.Canthaxanthin.A New Total Synthesis., J.Org.Chem., Vol 47, No.11, 2130-2134, 1982 reported the following The synthetic method described above. [0003] [0004] [0005] The above method uses the highly toxic triphenylphosphine and produces the equally highly toxic triphenylphosphine oxide in the last step of the reaction. In order to avoid the use of triphenylphosphine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/28C07C403/24
Inventor 皮士卿潘亚金李斌郑桂宁张美英
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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