Neohesperidin synthesis technology

Abstract

The invention relates to the field of organic synthesis and discloses a neohesperidin synthesis technology. The neohesperidin synthesis technology comprises the following steps of adding phloroacetophenone-4'-beta-neohesperidin and isovanillin (CAS: 621-59-0) as initial raw materials and a low-carbon alcohol solvent having the content of more than 98wt% into a three-necked flask, carrying out stirring for dissolution, feeding N2 into the three-necked flask to expel air in the three-necked flask, carrying out heating, orderly adding a main catalyst and a cocatalyst into the three-necked flask, carrying out timing at backflow starting time, stopping heating after the reaction lasts for 2-8h, carrying out cooling to a room temperature, carrying out filtration, washing the filter cake by a small amount of hot low-carbon alcohol, and carrying out vacuum drying at a temperature of 50 DEG C to obtain white solid neohesperidin powder. Compared with the existing neohesperidin synthesis technology, the neohesperidin synthesis technology provided by the invention has the advantages of low cost, high yield, high purity and small environmental pollution and is suitable for neohesperidin industrial production.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a synthesis process of neohesperidin. [0002] Background technique [0003] Neohesperidin is a dihydroflavonoid compound, which exists in small amounts in some Rutaceae plants (lime, sweet orange, Citrus aurantium, Citrus aurantium and Achilles chinensis, etc.) It is a glycoside formed by one hesperetin unit and one neohesperidose unit, that is, hesperetin-7-O-neeohesperidoside, and its structural formula is as follows: [0004] The most important use of neohesperidin in the medical field is in gastrointestinal drugs, which has the effects of reducing phlegm and eliminating stagnation, breaking qi and eliminating swelling. In addition, neohesperidin can be directly used as a sweetener in the food industry, and it is also useful in the tobacco industry to suppress tobacco miscellaneous gas in my country. At the same time, neohesperidin dihydrochalcone derived from ne...

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Problems solved by technology

The specific details of the second step of L-proline catalysis are not provided in this patent. In fact, the inventors cannot obtain neohesperidin by using the method described in this patent.

U.S. Patent No. 3,375,242 uses a one-step method to react directly with isovanillin in lye with naringin, and obtain neohesperidin after acidification. The shortcoming of this synthesis method is that the reaction yield is low, and the usage amount of isovanillin is too large , and isovanillin is not easy to recycle, it is easy to cause environmental pollution, and the cost of raw materials is also high, which is not conducive to industrial production

Thereafter, people such as Roberrison adopted a two-step method, wherein the second step of synthesis also reacted in lye to generate neohesperidin, and the reaction efficiency was also very low (see literature Ind. Eng. Chem., Prod. Res. Develop., Vol. 13, No. 2, 1974)

It can be seen that the classic basic catalyst for the aldol condensation reaction is not suitable for the synthesis reaction of neohesperidin, and this catalytic system is difficult to achieve industrial production

Therefore, when U.S. Patent No. 3947405 adopts a two-step method, the second step reaction is improved, that is, the root bark acetophenone-4'-β-neohesperidoside and isovanillin are reacted under a tetrahydropyrrole-acetic acid catalytic system to prepare To obtain neohesperidin, but the requirements for industrialization are relatively strict: 1) argon protection is required; 2) anhydrous alcohol solvents are required; 3) the reaction time is long; 4) the amount of tetrahydropyrrole is relatively large; 5) product purity not tall

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