Preparation method for 3-O-alkyl ascorbic acid

A technology of an alkyl ascorbic acid and a synthesis method, which is applied in the field of preparation of 3-O-alkyl ascorbic acid, can solve the problems of complex process products, complicated post-processing, unsuitable for large-scale production and the like, and achieves environmentally friendly process, simple and feasible process , the synthesis route is simple and novel effect

Inactive Publication Date: 2013-12-25
CHONGQING TECH & BUSINESS UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the products of one-step process are relatively complicated, and the p

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  • Preparation method for 3-O-alkyl ascorbic acid

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Embodiment 1

[0016] Under the protection of nitrogen, add 10.1 g (0.1 mol) of triethylamine to 50 ml of methanol, and slowly add 20.8 g (0.1 mol) of 2-keto-L-gulonate methyl ester to the above mixture under stirring. , Add 1 gram of molecular sieve, then add 12.6 grams (0.1 mol) of dimethyl sulfate dropwise, heat to 60 degrees and react for 3 hours, distill the methanol from the reaction solution under reduced pressure, and concentrate the viscous reaction solution in ethyl acetate After flushing, it quickly passes through a silica gel column (Flash column chromatography), and stops when the 2-keto-3-O-methyl-L-gulonate methyl ester is completely flushed out. Evaporate the solvent to obtain a yellow product. Under the protection of nitrogen, dissolve the obtained yellow product in 80 ml methanol, add 9.25 g (0.11 mol) sodium bicarbonate and 1.5 g (0.02 mol) calcium fluoride, reflux for 5 hours, and distill the methanol from the reaction solution under reduced pressure The concentrated visc...

Embodiment 2

[0018] Under the protection of nitrogen, add 10.1 g (0.1 mol) of triethylamine to 50 ml of ethanol, and slowly add 22.2 g (0.1 mol) of ethyl 2-keto-L-gulonate to the above mixture under stirring. , Add 1 gram of molecular sieve, and then add 15.4 grams (0.1 mol) of diethyl sulfate dropwise, heat to 78 degrees and react for 3 hours, distill the ethanol from the reaction solution under reduced pressure, and concentrate the viscous reaction solution in ethyl acetate After flushing, it quickly passes through a silica gel column (Flash column chromatography), and stops when the 2-keto-3-O-ethyl-L-gulonate ethyl ester is completely flushed out by the dot plate. Evaporate the solvent to obtain a yellow product. Under the protection of nitrogen, dissolve the obtained yellow product in 80 ml of ethanol, add 9.25 g (0.11 mol) of sodium bicarbonate and 1.5 g (0.02 mol) of calcium fluoride, reflux for 5 hours, and distill the ethanol from the reaction solution under reduced pressure The c...

Embodiment 3

[0020] Under nitrogen protection, add 10.1 g (0.1 mol) of triethylamine to 50 ml of ethanol, and slowly add 20.8 g (0.1 mol) of 2-keto-L-gulonate methyl ester to the above mixture under stirring. , Add 1 gram of molecular sieve, then add 22.2 grams (0.1 mol) of diethyl sulfate dropwise, heat to 78 degrees for 3 hours, distill the ethanol from the reaction solution under reduced pressure, and concentrate the viscous reaction solution in ethyl acetate After flushing, it quickly passes through a silica gel column (Flash column chromatography), and stops when the 2-keto-3-O-ethyl-L-gulonate methyl ester is completely flushed out. Evaporate the solvent to obtain a yellow product. Under the protection of nitrogen, dissolve the obtained yellow product in 80 ml of ethanol, add 9.25 g (0.11 mol) of sodium bicarbonate and 1.5 g (0.02 mol) of calcium fluoride, reflux for 5 hours, and distill the ethanol from the reaction solution under reduced pressure The concentrated viscous reaction s...

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Abstract

The invention discloses a preparation method for 3-O-alkyl ascorbic acid. The preparation method comprises the steps that under protection of nitrogen, 2-keto-L-gulonic acid ester reacts with sulfuric acid diester at the presence of catalyst molecular sieves, and an obtained intermediate under the action of sodium bicarbonate and calcium fluoride generates the 3-O-alkyl ascorbic acid. According to the preparation method, a synthetic route is simple, a synthetic method is novel, a process is easy and convenient to achieve, postprocessing is simple, the yield and purity of products are high, catalysts are low in price and easy to obtain, the environment is not affected, and the preparation method is suitable for industrial production.

Description

Technical field [0001] The invention relates to a preparation method of 3-O-alkyl ascorbic acid. Background technique [0002] Vitamin C (that is, L-ascorbic acid) has attracted much attention from the chemical, medical, and nutritional circles since it was successfully synthesized in the 1930s. It has played an important role in cosmetics, food additives, medicine and health care and other fields. Vitamin C can promote the synthesis of cellular collagen, improve skin tension and reduce wrinkles. It also has a good auxiliary effect on eliminating freckles and age spots. Although vitamin C has high activity, it is unstable and easily damaged by light, heat, oxygen, etc. and loses its reducing ability. This instability greatly reduces its utilization efficiency and commercial value in cosmetics and other industries. [0003] 3-O-alkyl ascorbic acid is a very useful vitamin C derivative. It is not only chemically stable, it is a vitamin C derivative that does not change color, but ...

Claims

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Application Information

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IPC IPC(8): C07D307/62
Inventor 蒋和雁
Owner CHONGQING TECH & BUSINESS UNIV
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