Preparation method of chrysanthemic acid with high optical purity
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A pure chrysanthemic acid, optical technology, applied in the field of chemistry, can solve the problem of no dexamine available for purchase, and achieve the effects of easy operation, short split operation period and low energy consumption
Inactive Publication Date: 2010-09-15
SHANDONG UNIV OF TECH
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The Chloramphenicol market is gradually shrinking with global restrictions on Chloramphenicol production and production bans are likely in the nea...
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Embodiment 1
[0021] 1) 21.6 grams of hydrochloride of ethyl D-phenylglycine was dissolved in 100 milliliters of water at 25°C, adjusted to pH 8 with sodium bicarbonate, and a mixture of 33.6 grams of trans-chrysanthemic acid and 100 milliliters of toluene was added. solution, fully stirred for 30 minutes, and centrifuged to collect the precipitated D-phenylglycine ethyl ester trans-dexychrysanthemic acid double salt;
[0022] 2) The obtained double salt was placed in an aqueous hydrochloric acid solution at pH 2, stirred for 30 minutes, and allowed to stand for stratification to obtain 13.6 grams of trans-D-chrysanthemic acid with an optical purity of 90%, which was 81% of the theoretical yield;
[0023] 3) The acid solution of the resolving agent D-type phenylglycinate was adjusted to pH 7 with sodium carbonate, and 15.6 grams of the resolving agent was recovered, and the recovery rate of the resolving agent was 87%.
Embodiment 2
[0025] Using D-phenylglycine methyl ester hydrochloride as a resolving agent and operating under the same conditions as in Example 1, 12.8 g of trans-D-chrysanthemic acid with an optical purity of 90% was obtained, which was 76% of the theoretical yield. 13.8 grams of resolving agent were reclaimed, and the resolving agent recovery rate was 77%.
Embodiment 3
[0027] Using D-phenylglycine isopropyl hydrochloride as a resolving agent and operating under the same conditions as in Example 1, 13.8 g of trans-D-chrysanthemic acid with an optical purity of 86% was obtained, which was 82% of the theoretical yield. 15.9 grams of resolving agent were reclaimed, and the recovery rate of resolving agent was 89%.
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Abstract
The invention discloses a preparation method of chrysanthemic acid with high optical purity. The preparation method is characterized by comprising the following steps of: (1) forming a double salt of trans-dextrotatory chrysanthemic acid phenylglycine butyl ester from trans-dl chrysanthemic acid and a resolving agent of D type phenylglycine butyl ester or hydrochloride of the resolving agent of D type phenylglycine butyl ester in a solvent system; (2) acidizing the double salt obtained from the step (1), standing and dimixing, wherein the upper layer is the trans-dextrotatory chrysanthemic acid with high optical purity and the lower layer is an acid solution of the resolving agent of D type phenylglycine butyl ester; and (3) obtaining a trans-dextrotatory chrysanthemic acid product by separation, neutralizing the acid solution of the D type phenylglycine butyl ester with alkali and recovering the resolving agent. The preparation method has the advantages of easy operation, high resolving speed, short operation period, high selectivity and low energy consumption.
Description
technical field [0001] The invention relates to a method for preparing chrysanthemic acid with high optical purity, belonging to the technical field of chemistry. Background technique [0002] At present, the active ingredients widely used in household sanitation insecticides are pyrethroids represented by allethrin, which are highly efficient and low in toxicity, and are harmless to humans and animals. The key intermediate for the synthesis of such insecticides is chrysanthemic acid , it has a variety of isomers, among which the permethrin ester formed by trans chrysanthemic acid has the highest insecticidal effect, and the common method to obtain trans chrysanthemic acid is to separate and obtain it . Such as: (R)-(+)-1-amino-1,4a-dimethyl-7-isopropyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (South China Journal of Polytechnic University, 27 (3), 100-105, 1999), L-lysine (German patent 2043137, 1971), ephedrine (European patent 68736, 1981), (-)-cis-benzyl-( 2-hydroxym...
Claims
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