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A kind of preparation method of vitamin c ethyl ether

A vitamin and ethyl ether technology, applied in the direction of organic chemistry, can solve the problems of high toxicity and pollution, difficult separation, and many impurities, and achieve the effect of high product yield and purity

Active Publication Date: 2022-08-09
SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The one-step method not only alkylates the 3-hydroxyl group, but also the 5- and 6-position hydroxyl groups, resulting in more impurities, difficult separation and low yield
The three-step method can protect the 5 and 6 hydroxyl groups from being alkylated, and the reaction generates less impurities; however, the solvent for the alkylation reaction is DMSO or DMF, and the product is highly soluble in the solvent, and the product yield is low and post-processing is difficult. Halogenated alkanes or diethyl sulfate are used as alkylating reagents, which are more toxic and polluting

Method used

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  • A kind of preparation method of vitamin c ethyl ether
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Experimental program
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Effect test

Embodiment 1

[0021] Synthesis of Intermediate 1

[0022] Add vitamin C (25kg, 142mol) and cyclopentanone (175kg) into the 500L reaction kettle, stir at room temperature, slowly add acetyl chloride (11.1kg, 142mol) dropwise, finish dropping, react at 25°C for 4h; suction filtration, cyclopentanone The filter cake was rinsed to obtain 31.6kg of white solid with a yield of 92% and a purity of 98.34%.

Embodiment 2

[0024] Synthesis of Intermediate 2

[0025] Add ethanol (150kg) into the 500L reaction kettle, cool down and stir to 0~5°C, add thionyl chloride (22.1kg, 186mol) dropwise, stir at 0~5°C for 1h, add Intermediate 1 (30kg, 124mol) It was added to the reaction flask, and triethylamine (18.8kg, 186mol) was added dropwise at 0~5°C. After the drop was completed, the mixture was heated and stirred to reflux for 12 hours, and the solvent was evaporated to dryness under reduced pressure to obtain an off-white solid. Ethyl acetate (240kg) and water (150kg) were added to the obtained solid and stirred at room temperature for 0.5h, the liquid was separated, the organic phase was evaporated to remove about 170kg of solvent, cooled to 0~5°C, stirred and crystallized for 2h, suction filtered, and a small amount of ethyl acetate was rinsed. The filter cake was washed to obtain 28.9kg of off-white solid with a yield of 86.3% and a purity of 98.84%.

Embodiment 3

[0027] Synthesis of Vitamin C Ethyl Ether

[0028] Intermediate 2 (27kg, 100mol) and 3mol / L hydrochloric acid (216kg) were successively added to the there-necked flask of the 500L reaction kettle, heated and stirred to 50~60°C, incubated for 2h, and the solvent was evaporated to dryness under reduced pressure to obtain a yellow oil. ; Add ethanol (135kg), heat and stir until the oil dissolves, add activated carbon (1.35kg), reflux for 0.5h, hot filter, cool the filtrate to -5~0℃, stir and crystallize for 2h, suction filtration, rinse and filter with cold ethanol cake to obtain 16.3kg of white solid, the yield is 80.1%, and the purity is 99.15%. ESI-MS(C 8 H 12 O 6 ,m / z) Measured value (calculated value): 204.1(204.06)[M-H] － . 1 H-NMR (400MHz, MeOH-d 4 ): 1.28(t, 3H), 3.65(m, 2H), 3.90~3.92(m, 1H), 4.45(m, 2H), 4.79(d, 1H).

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Abstract

The invention relates to a preparation method of vitamin C derivatives, in particular to a preparation method of vitamin C ethyl ether. The method takes vitamin C as the starting material, first reacts with cyclopentanone to form ketal, then reacts with ethanol and thionyl chloride to form ether, and finally hydrolyzes the ketal with hydrochloric acid to obtain vitamin C ethyl ether. The method has easily available raw materials, simple operation, environmental protection, low cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of vitamin C ethyl ether, belonging to the field of cosmetic raw material synthesis. Background technique [0002] Vitamin C is one of the strongest antioxidants in nature, which can capture free radicals, protect cells and tissues, and resist the damage caused by free radicals and reactive oxygen species. Due to the disadvantages of low lipophilicity, heat sensitivity, and auto-oxidative degradation of vitamin C, its application is limited. Therefore, many vitamin C derivatives that improve their properties have emerged, such as the widely used vitamin C phosphate magnesium, vitamin C palmitate and so on. Vitamin C ethyl ether is a new lipophilic and hydrophilic amphoteric vitamin C derivative, which can be very convenient to use in the formula. It can easily penetrate the stratum corneum of the skin and enter the dermis layer. After entering the skin, it is easily decomposed by biological enzymes. The b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/62
CPCC07D307/62
Inventor 李新志张彬孔祥雨崔新强杨利刘文涛毋立华纪红英冯巧巧王洪臣魏乐坤郑德强
Owner SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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