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Preferential Crystallization Resolution of Racemic 1,1'-Bi-2-Naphthol

A technology with preferential crystallization and racemization, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc.

Active Publication Date: 2016-10-19
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

[0002] Preferential crystallization is a traditional racemate resolution method, which is simple to operate and low in cost, but it is only suitable for the resolution of racemic mixtures (Conglomerate, Congl.) that can form aggregates

Method used

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  • Preferential Crystallization Resolution of Racemic 1,1'-Bi-2-Naphthol
  • Preferential Crystallization Resolution of Racemic 1,1'-Bi-2-Naphthol
  • Preferential Crystallization Resolution of Racemic 1,1'-Bi-2-Naphthol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Dissolve 0.5000g each of R-BINOL and S-BINOL in 10mL methanol, add 0.1930g Me 4 NCl, heated and stirred to make Me 4 After the NCl is completely dissolved, continue to heat to boiling, and stand for crystallization for 48 hours to obtain 0.6027g and 0.6122g of R-BINOL Me 4 NCl and S-BINOL·Me 4 NCl seeds with yields of 86.97% and 88.34%.

[0017] Combine 5.70g rac-BINOL and 2.20g Me 4 Add NCl to 70mL methanol, heat and stir until racemic BINOL and Me 4 After NCl is completely dissolved, continue heating to boiling, filter while hot, add 3.0mg R-BINOL·Me to the filtrate after cooling to room temperature 4 NCl seed crystal, stirred and crystallized for 16h to obtain the product R-BINOL·Me 4 NCl 0.83g; added racemic BINOL·Me 4 NCl 0.83g and add methanol to a total volume of 70mL, heat and stir until racemization of BINOL and Me 4 After NCl is completely dissolved, continue heating to boiling, add 3.0mg S-BINOL·Me to the filtrate after cooling to room temperature 4 N...

Embodiment 2

[0020] Dissolve 1.0000g each of R-BINOL and S-BINOL in 20mL methanol, add 0.3860g Me 4 NCl, heated and stirred to make Me 4 After the NCl is completely dissolved, continue to heat to boiling, and stand for crystallization for 48 hours to obtain 1.2014g and 1.2490g of R-BINOL Me 4 NCl and S-BINOL·Me 4 NCl seeds with yields of 86.68% and 90.12%.

[0021] 11.40g racemic BINOL and 4.40g Me 4 Add NCl to 140mL methanol, heat and stir until racemic BINOL and Me 4 After NCl is completely dissolved, continue heating to boiling, filter while hot, add 6.0mg R-BINOL·Me to the filtrate after cooling to room temperature 4 NCl seed crystal, stirred and crystallized for 16h to obtain the product R-BINOL·Me 4 NCl 1.76g; supplemented with rac BINOL·Me 4 NCl 1.76g and add methanol to a total volume of 140mL, heat and stir to make racemization of BINOL and Me 4 After NCl is completely dissolved, continue heating to boiling, add 6.0mg S-BINOL·Me to the filtrate after cooling to room tempera...

Embodiment 3

[0024] Dissolve 1.5000g each of R-BINOL and S-BINOL in 30mL methanol, add 0.5790g Me 4 NCl, heated and stirred to make Me 4 After the NCl is completely dissolved, continue to heat to boiling, and stand for crystallization for 48h to obtain 1.8680g and 1.9012g of R-BINOL Me 4 NCl and S-BINOL·Me 4 NCl seeds with yields of 89.85% and 91.45%.

[0025] 17.10g racemic BINOL and 6.60g Me 4 Add NCl to 210mL methanol, heat and stir until racemic BINOL and Me 4 After NCl is completely dissolved, continue to heat to boiling, filter while hot, add 9.0mg R-BINOL·Me to the filtrate after cooling to room temperature 4 NCl seed crystal, stirred and crystallized for 16h to obtain the product R-BINOL·Me 4 NCl 2.01g; added racemic BINOL·Me 4 NCl 2.01g and add methanol to a total volume of 210mL, heat and stir to make racemization of BINOL and Me 4 After NCl is completely dissolved, continue heating to boiling, add 9.0mg S-BINOL·Me to the filtrate after cooling to room temperature 4 NCl s...

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Abstract

The invention discloses a simple chiral splitting method of racemic 1,1'-unite-2-naphthol. The method comprises the step of: adding R-BINOL.Me4NCl and S-BINOL.Me4NCl seed crystals to a mixed solution of saturated or supersaturated racemic BINOL and Me4NCl in a cycle, so that an enantiomer is excessive a little, and does not cause an asymmetric environment. Thus, an isomer as the same as the seed crystal in chirality is crystallized from the solution; and the R-BINOL and S-BINOL of which the e.e. value is greater than 99% can be separately obtained by recrystallization and dissociation. The method is simple to operate, low in cost, green and environment-friendly; and binaphthol with high enantiomeric purity can be obtained.

Description

technical field [0001] The invention relates to a resolution method of chiral compounds, in particular to a green and simple chiral resolution method of racemic 1,1'-bi-2-naphthol. Background technique [0002] Preferential crystallization is a traditional method for the resolution of racemates. It is simple to operate and low in cost, but it is only suitable for the resolution of racemic mixtures (Conglomerate, Congl.) that can form aggregates. Although racemic BINOL itself is a racemic compound, studies have shown that by adding tetramethylammonium chloride of equimolar mass to the methanol solution of racemic BINOL, two inclusion complexes can be obtained at different concentrations, respectively. Literature reports have confirmed that one of the inclusion complexes is a racemic aggregate Congl., while the other is a racemic compound (Yoshizawa K, Toyota S, Toda F. Tetrahedron, 2004, 60: 7767-7774) . Therefore, we can use the preferential crystallization method to induc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/86C07C39/14
Inventor 孙果宋陈渊川阮恒韦志明章慧郑明贤刘宇宏张燕娟
Owner GUANGXI RES INST OF CHEM IND CO LTD
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