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A technology of dimethoxy, cumene, applied in the field of pharmacy, can solve problems such as inability to achieve mass production, inability to obtain purity, and difficulty in separation
Active Publication Date: 2016-04-06
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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[0009] 3,5-Dimethoxy-4-isopropylphenylacrylic acid is the main impurity in the preparation of (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylphenyl)acrylic acid , and because it contains a carboxyl group, its polarity is relatively large, its structure is similar to that of (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylbenzene)acrylic acid, and its chemical properties are relatively similar. The two cannot be separated very well, and the method of multiple recrystallizations not only reduces the loss of (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylphenyl)acrylic acid It is large and cannot obtain (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylphenyl)acrylic acid with a purity greater than 95%. Only a small amount can be obtained by column chromatography (E)-2-Phenyl-3(3,5-dimethoxy-4-isopropylphenyl)acrylic acid
And the method that adopts column chromatography can't realize mass production, is not suitable for the use of industrialized production; If the impurity in the condensation is not removed, after the reaction of decarboxylation and demethylation, generate corresponding 3,5-dimethoxy -4-isopropylstyrene and 3,5-dihydroxy-4-isopropylstyrene, its structure is similar to the product to be separated, and the similar properties make separation more difficult, so that the final target product yield is greatly improved reduce
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[0042] Example 1 A purification method of (E)-2-phenyl-3 (3,5-dimethoxy-4-isopropylbenzene) acrylic acid
[0043] A method for purifying (E)-2-phenyl-3 (3,5-dimethoxy-4-isopropylbenzene) acrylic acid, which comprises two steps:
[0044] The first step is to selectively esterify (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylbenzene)acrylic acid with a purity of 80% to obtain a purity of 90% % of (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylphenyl)acrylic acid a; react according to the following equation:
[0045]
[0046] Follow the steps below in order:
[0047] 10 g of crude (E)-2-phenyl-3 (3,5-dimethoxy-4-isopropylbenzene) acrylic acid with a purity of 80% (its HPLC diagram is shown in Figure 5 Shown) was added to 60mL of isopropanol and stirred to dissolve, then 0.1g of concentrated sulfuric acid was added dropwise, and the temperature was raised to 60°C. After reacting for 5 hours, cooled to room temperature, the alcohol solvent isopropanol was removed, and ether and saturated ...
Embodiment 2-6
[0056] The purification method of embodiment 2-6 (E)-2-phenyl-3 (3,5-dimethoxy-4-isopropylbenzene) acrylic acid
[0057] Examples 2-6 are respectively a purification method of (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylbenzene)acrylic acid, similar to the purification method of Example 1, The only difference is that the technical parameters involved are different, and the specific differences are shown in the following table:
[0058]
[0059] Note: Substance A in the above table represents (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylphenyl)acrylic acid; substance Aa represents (E)-2-phenyl- 3(3,5-Dimethoxy-4-isopropylphenyl)acrylic acid a; Substance A product represents the final (E)-2-phenyl-3(3,5-dimethoxy-4 - cumene) acrylic products.
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Abstract
The invention discloses a purifying method of (E)-2-phenyl-3-(3,5-dimethoxy-4-isopropyl benzene) crylic acid and comprises two steps: 1, carrying out selective esterification on (E)-2-phenyl-3-(3,5-dimethoxy-4-isopropyl benzene) crylic acid with purity of 80-85% to obtain (E)-2-phenyl-3-(3,5-dimethoxy-4-isopropyl benzene) crylic acid a with purity of 90-95% and generating corresponding esters from impurity acids, wherein a very small quantity of corresponding esters are generated under the same reaction conditions since the product has relatively large steric hindrance and therefore the selective esterification effect is achieved; and 2, carrying out recrystallizing reaction, wherein a proper recrystallizing reagent is used and (E)-2-phenyl-3-(3,5-dimethoxy-4-isopropyl benzene) crylic acid with purity of 99% or above can be obtained. The method is applicable to purification of (E)-2-phenyl-3-(3,5-dimethoxy-4-isopropyl benzene) crylic acid and is further applicable to preparation of cis-2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol.
Description
technical field [0001] The invention belongs to the field of pharmacy, and relates to a method for purifying a cis-phenylene moder intermediate, in particular to (E)-2-phenyl-3(3,5-dimethoxy-4-isopropyl Benzene) Purification method of acrylic acid. Background technique [0002] Benvitimod is a new generation of anti-inflammatory drugs that can be used to treat a variety of major autoimmune diseases, such as psoriasis, eczema, pyogenic colitis and various allergic diseases. Synthetic phenymod products are usually accompanied by the presence of cis-isomer impurities. [0003] Chinese invention patent application CN103992212A discloses a "synthetic method of cis-phenylene moder and application of cis-styrene moder" and provides a synthetic method of cis-styryl moder, with 3,5-dihydroxy- 4-isopropylbenzoic acid is used as raw material, and (E)-2-phenyl-3(3,5-dimethoxy-4-isopropylbenzene is prepared by methylation, reduction, oxidation and condensation methods ) crude product ...
Claims
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