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Synthesizing method of vitamin C ethyl ether

A synthesis method and vitamin technology, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of physical injury of production workers, prolonged production sections, unfavorable environmental protection, etc., achieve high equipment utilization, reduce material transfer, supply Good stability effect

Active Publication Date: 2015-07-08
ZHEJIANG APELOA KANGYU PHARMA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition to acetone, the centrifuge mother liquor also contains a large amount of water (about 3%), hydrogen chloride, acetic acid and other impurities, which are not easy to recycle and reuse, resulting in a large amount of industrial waste liquid
In the second step, the crude product needs to be recrystallized with highly toxic benzene, which will cause physical harm to production workers and is not conducive to environmental protection.
Although the yield is high, the catalyst must be prepared in advance, prolonging the production process, and the product needs to be recrystallized by ethyl acetate / n-hexane (1:1)

Method used

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  • Synthesizing method of vitamin C ethyl ether
  • Synthesizing method of vitamin C ethyl ether
  • Synthesizing method of vitamin C ethyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A synthetic method of vitamin C ethyl ether, comprising the steps of:

[0043] (1) (R)-3,4-dihydroxy-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]furan-2(5H)-one preparation of

[0044] ①In a 30L reaction flask, under mechanical stirring and nitrogen protection, add 3.42 kg vitamin C, 2.22 kg acetone dimethyl acetal and 11.23 kg dimethyl sulfoxide, heat to 30°C and stir;

[0045] ② Add 33.4 g of catalyst p-toluenesulfonic acid and keep it warm for 180 minutes;

[0046] ③The external temperature was 40°C, and methanol and a small amount of unreacted acetone dimethyl acetal were distilled off under reduced pressure. Obtain the DMSO solution of the product of step (1). Go directly to the next reaction.

[0047] After detection, the product is (R)-3,4-dihydroxy-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]furan-2(5H) - Ketone, HPLC purity ≥ 97%, mp.=208-210°C. 1 HNMR (400MHz, DMSO-d 6 ) δ (ppm): 1.23 (6 H, s), 3.86-3.88 (1H, dd, J=6.3, 8.4Hz), 4.05-4.09 (1 H, dd, J=7.0, 8.4Hz), 4....

Embodiment 2

[0058] A synthetic method of vitamin C ethyl ether, comprising the steps of:

[0059] (1) (R)-3,4-dihydroxy-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]furan-2(5H)-one preparation of

[0060] ①In a 30L reaction flask, under mechanical stirring and nitrogen protection, add 3.42 kg vitamin C, 2.22 kg acetone dimethyl acetal and 11.23 kg dimethyl sulfoxide, heat to 30°C and stir;

[0061] ② Add 48.7 g catalyst pyridinium p-toluenesulfonate and keep warm for 180 minutes;

[0062] ③The external temperature was 40°C, and methanol and a small amount of unreacted acetone dimethyl acetal were distilled off under reduced pressure. Obtain the DMSO solution of the product of step (1). Go directly to the next reaction.

[0063] After detection, the product is (R)-3,4-dihydroxy-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]furan-2(5H) - Ketone, HPLC purity ≥ 97%, mp.=208-210°C.

[0064] (2) (R)-4-ethoxy-3-hydroxy-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]furan-2(5H ) - Preparation of ketones

[0065]...

Embodiment 3

[0074] Other conditions are the same as in Example 1, the difference is that (R)-4-ethoxy-3-hydroxyl-5-[(S)-2,2-dimethyl-1,3 In the step of -dioxolan-4-yl]furan-2(5H)-one, 3.289 kg of bromoethane was put into the step and reacted for 8 hours. The total yield of the two steps was 65% (calculated as vitamin C).

[0075] After detection, the product is (R)-4-ethoxy-3-hydroxy-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]furan-2 (5H)-ketone, HPLC purity ≥94%, mp. =104-106℃.

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Abstract

The invention relates to the field of the synthesis of vitamin C derivatives, and in particular relates to a synthesizing method of vitamin C ethyl ether. The method comprises the following steps of: reacting vitamin C as an initiative raw material and dimethoxy propane as a reactant, thereby generating (R)-3,4-dyhydroxyl-5- [(S)-2,2-dimethyl-1,3-dioxolane-4-yl] furan-2(5H)-ketone; next, adding alkali and an alkylation reagent, thereby generating (R)-4-ethyoxyl-3-hydroxyl-5-[(S)-2,2-dimethyl-1,3-dioxolane-4-yl] furan-2(5H)-ketone; and removing a protecting group, thereby generating the vitamin C ethyl ether. According to the method, the reactions in the three steps can be finished in the same kettle, so that the industrialized operation is simplified greatly; and a large number of organic waste liquids cannot be generated. As a result, the total yield in the three steps is improved to 50%-53.4%.

Description

technical field [0001] The invention belongs to the field of cosmetic chemistry, relates to the field of synthesis of vitamin C derivatives, in particular to a vitamin C ethyl ether (3-O-ethyl ascorbyl ether, 3-O-Ethyl Ascorbyl Ether, CAS: 86404-04-8, That is, the synthesis method of (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-ethoxyl-3-hydroxyl-5H-furan-2-one. Background technique [0002] Because vitamin C has 4 hydroxyl groups in its structure, it cannot be directly absorbed by the skin, and it is easily oxidized to cause discoloration. As a whitening agent, its use in cosmetics is limited. The vitamin C ethyl ether (compound shown in formula I) obtained after the 3-hydroxyl is alkylated is a vitamin C derivative that does not change color and does not affect its biological activity, thus filling the gap in the market for similar products. Studies have shown that vitamin C ethyl ether is easily decomposed by enzymes after entering the skin to play the role of vitamin C. [0003]...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/62
CPCY02P20/55
Inventor 孙光刘思宏冯立春吴斌郭振荣
Owner ZHEJIANG APELOA KANGYU PHARMA
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