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Resolving agent for 1, 1'-bi-2-naphthol and resolving method thereof

A resolving agent and technology of binaphthol, which is applied in the field of resolving agent and resolution of 1,1'-bin-2-naphthol, can solve the high cost of binaphthol resolution and unstable chemical properties , low splitting efficiency and other issues, to achieve the effect of high splitting efficiency, easy control of reaction conditions, and easy recycling

Active Publication Date: 2009-11-18
GUANGXI RES INST OF CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these resolving agents have the defects of poor sources, high price, or unstable chemical properties, or low recovery rate, difficult purification, or low resolution efficiency, which leads to the high cost of binaphthol resolution.

Method used

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  • Resolving agent for 1, 1'-bi-2-naphthol and resolving method thereof
  • Resolving agent for 1, 1'-bi-2-naphthol and resolving method thereof
  • Resolving agent for 1, 1'-bi-2-naphthol and resolving method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 2.85 grams (0.01 mol) of optically active resolving agent (+)-dehydroabietylamine and 2.86 gram (0.01 mol) of racemic 1,1 '-linked-2-naphthol are dissolved in 30 milliliters of 80% ( V 甲醇 / V 水 ) in methanol aqueous solution, heated to reflux for 6 hours, cooled to -15°C, and white crystal S-(-)-binaphthol dehydroabietylamine salt was precipitated. After filtration, the mother liquor contains R-(+)-binaphthol dehydroabietylamine salt, which is collected for future use. The filter cake was treated with 30 milliliters of 5% potassium hydroxide aqueous solution, and the light yellow resolving agent (+)-dehydroabietylamine was separated out, and the (+)-dehydroabietylamine was extracted with 30 milliliters of toluene, and the toluene organic layer was collected for subsequent use. The water layer was neutralized to neutral with 5% sulfuric acid, and the white crystal S-(-)-binaphthol was precipitated, filtered, washed with distilled water, dried, and recrystallized with a ...

Embodiment 2

[0046] The mother liquor containing R-(+)-binaphthol dehydroabietylamine salt obtained in Example 1 was concentrated by distillation, and the methanol solvent was recovered. The distillation residue was treated with 30 ml of 5% potassium hydroxide aqueous solution, and the light yellow resolving agent (+)-dehydroabietylamine was separated out, and the (+)-dehydroabietylamine was extracted with 30 ml of toluene, and the toluene organic layer was collected for subsequent use , the water layer was neutralized to neutral with 5% sulfuric acid, and the white crystal R-(-)-binaphthol was precipitated, filtered, washed with distilled water, dried, and recrystallized with a small amount of toluene to obtain R-(+)- Binaphthol 1.02 g (yield 71%), melting point: 208 ° C ~ 210 ° C, [a] D 20 =+35.2° (C=1, THF), optical purity (ee value): 99.2%.

Embodiment 3

[0048] 5.70 g (0.02 mol) of optically active resolving agent (+)-dehydroabietylamine and 2.86 g (0.01 mol) of racemic 1,1'-linked-2-naphthol were dissolved in 40 ml of isopropyl In alcohol, heat to reflux for 1 hour, add 6 ml of water, cool to -10°C, and white crystal S-(-)-binaphthol dehydroabietylamine salt is precipitated. After filtration, the mother liquor contains R-(+)-binaphthol dehydroabietylamine salt, which is collected for future use. The filter cake was treated with 30 milliliters of 5% sodium hydroxide aqueous solution, and the light yellow resolving agent (+)-dehydroabietylamine was separated out, and the (+)-dehydroabietylamine was extracted with 30 milliliters of toluene, and the toluene organic layer was collected for subsequent use. The water layer was neutralized to neutral with 5% hydrochloric acid, and the white crystal S-(-)-binaphthol was precipitated, filtered, washed with distilled water, dried, and recrystallized with a small amount of toluene to obt...

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Abstract

The invention provides a resolving agent for racemized 1, 1'-bi-2-naphthol and a resolving method thereof. The resolving agent is a dehydroabietylamine. The resolving method comprises the following steps of: leading the racemized 1, 1'-bi-2-naphthol and optically pure resolving agent (+)-dehydroabietylamine to react in a solvent to generate a diastereomer salt; carrying out the separation by utilizing the difference of solubility in the selected solvent; subsequently carrying out dissolving and purifying, thus obtaining the optically active 1, 1'-bi-2-naphthol single enantiomer. The method hashigh resolving efficiency, simple operation, short process flow, economic resolving method and low cost, the resolving agent (+)-dehydroabietylamine has easy source and low price, is easy to be reclaimed, has high reclaiming rate and can be used repeatedly.

Description

technical field [0001] The present invention relates to a process for the preparation of two optically active enantiomers of 1,1'-bi-2-naphthol. Background technique [0002] Binaphthol is a typical chiral compound (as shown in the following structure), which has strong surface asymmetry and can be used to prepare high-efficiency chiral catalysts, chiral inducers, etc., and plays a very important role in organic asymmetric synthesis. It plays an important role and is widely used in chiral medicine, pesticides and other fields. [0003] [0004] (S)-(-)-1,1'-bi-2-naphthol (R)-(+)-1,1'-bi-2-naphthol [0005] Due to the rich source of raw materials for the synthesis of racemic binaphthol, simple process, high product purity, and low price, chemical resolution is still the main method for mass production of single enantiomers of binaphthol. [0006] There are many chemical resolution methods for binaphthol, because the phenolic hydroxyl group of binaphthol has weak acidity,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/26C07C209/86C07C209/46C07C39/14C07C37/68
Inventor 黄春林戴日强
Owner GUANGXI RES INST OF CHEM IND CO LTD
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