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Method for synthesizing pentadecane triphenyl phosphonium salt

A technology of pentadecanetriphenyl and synthesis method, applied in the field of synthesis of pentadecatriphenylphosphine salt, can solve problems such as long reaction route, low yield, influence on large-scale production and the like

Inactive Publication Date: 2008-03-26
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The reaction route of the above method is long, and the yield is not high, which affects the large-scale production

Method used

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  • Method for synthesizing pentadecane triphenyl phosphonium salt
  • Method for synthesizing pentadecane triphenyl phosphonium salt
  • Method for synthesizing pentadecane triphenyl phosphonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: C 9 Preparation of Units (2,2,4,6,6-Pentamethyl-7,7a-dihydro-6H-benzo[1,3]dioxol-5-one)

[0026] 170 g (1.0 mol) of crystalline 3,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-one were suspended in 500 ml of dichloromethane. To this suspension are initially added 500 mg (2.9 mmol) p-toluenesulfonic acid and then 144 g (2.0 mol) vinyl ethyl ether at room temperature (RT) over a period of 2 hours. The mixture was then stirred at room temperature for 4 h, after which 100 ml of 5% strength sodium hydroxide solution were added. The lower organic phase was separated off, the aqueous phase was extracted once with 100 ml of dichloromethane, the combined organic phases were washed with 200 ml of water and concentrated on a rotary evaporator. The residue was dried under reduced pressure (oil pump) to give 2,2,4,6,6-pentamethyl-7,7a-dihydro-6H-benzo[1,3]dioxolane En-5-one, as a yellow oil, was pure by thin layer chromatography (TLC) and nearly pure by gas chromatography...

Embodiment 2

[0027] Embodiment 2: preparation compound 3

[0028] The C that embodiment 1 makes 9 Unit 21.5 grams (0.1mol, 98%) and compound 121g (0.12mol, 96%) were stirred in a 250ml three-necked flask with 50ml of n-hexane, the temperature was -10°C, nitrogen was blown, and 4.2N butyllithium was slowly added dropwise 36ml (0.15mol) of n-hexane solution, keeping the reaction temperature at about -10°C to -5°C, the dropwise addition was completed in 30 minutes, continued to stir for 1 hour, and tracked and detected by thin layer chromatography (TLC), C 9 The unit has reacted completely, warmed up to room temperature, added 50ml of water and stirred, separated, the aqueous phase was washed twice with 50ml of n-hexane, merged into the organic phase, and the organic phase was washed with 100ml of dilute acid water until neutral. The organic phase was concentrated under reduced pressure in a water bath at 50°C to obtain 45.2 g of a light red oil. The light red oil was subjected to high vacu...

Embodiment 3

[0029] Embodiment 3: preparation compound 4

[0030] The C that embodiment 1 makes 9 Unit 21.5 grams (0.1mol, 98%) and compound 2 21g (0.12mol, 96%) were stirred in a 250ml three-necked flask with 50ml of n-hexane, the temperature was -10°C, nitrogen was blown, and 4.2N butyl was slowly added dropwise. Lithium n-hexane solution 36ml (0.15mol), keep the reaction temperature at about -10°C ~ -5°C, add dropwise in 30 minutes, continue to stir for 1 hour, track and detect with thin layer chromatography (TLC), C 9 The unit has reacted completely, warmed up to room temperature, added 50ml of water and stirred, separated, the aqueous phase was washed twice with 50ml of n-hexane, merged into the organic phase, and the organic phase was washed with 100ml of dilute acid water until neutral. The organic phase was concentrated under reduced pressure in a water bath at 50°C to obtain 45.5 g of a light red oil. The light red oil was subjected to high vacuum (90-100Pa), the oil temperature...

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Abstract

The present invention provides improved synthesis process of pentadecyl triphenyl phosphonate as one important astaxanthin intermediate. The process prepares pentadecyl triphenyl phosphonate in an alcohol-concentrated sulfuric acid system directly without deprotection. The process of the present invention has less reaction steps and short reaction time, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of pentacarbontriphenylphosphine salt. Background technique [0002] Astaxanthin is a non-vitamin A carotenoid, which is widely used in the production of health products, medicines, cosmetics, food and feed additives. In food, it can not only be used for coloring, but also can effectively keep fresh and prevent discoloration, taste and deterioration. It can also be used for coloring of beverages, foods, seasonings, etc. Astaxanthin has a bright color and can be combined with actin non-intentionally. It is widely used in aquaculture feed, which can improve the skin and muscle color of farmed fish and increase the disease resistance of fish and shrimp. [0003] There are two methods for the production of astaxanthin, one is fermentation extraction and the other is chemical synthesis. Due to the small output and high cost of the fermentation extractio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/24C07F9/50
Inventor 劳学军沈润溥耿伟叶伟东
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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