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Method for preparing chiral binaphthalene diol

A technology of binaphthol and chirality, which is applied in the field of preparation of chiral binaphthol, can solve the problems of high price and high purity of resolving agent, and achieve the effects of fast reaction speed, economical method and simple operation

Inactive Publication Date: 2006-05-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The advantage of this method is that the yield is high and the purity is good. The disadvantage is that the derivatization and derivatization are carried out under strict anhydrous and oxygen-free conditions, and the resolution agent used is very high in purity and expensive.

Method used

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  • Method for preparing chiral binaphthalene diol
  • Method for preparing chiral binaphthalene diol

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Under stirring, dissolve 1.00 g of racemic 1,1'-binaphthyl-2,2'-diphenol in 10 ml of 6% sodium hydroxide solution, cool to room temperature, and add 0.20 g of tetrabutyl Ammonium bromide and 10.0 milliliters of dichloromethane, stir rapidly, add 1.04 milliliters of menthyl chloroformate (80.9%, 1.39 equivalents), keep room temperature and react for 8 minutes, stand still, separate the organic layer, and extract the water layer with dichloromethane , combined organic layers, washed with 3 × 10 ml of water, dried over anhydrous sodium sulfate, and removed the solvent by rotary evaporation to obtain a viscous liquid, which was dissolved with a small amount of dichloromethane and passed through a short column. Silica gel was the stationary phase, 5 cm long, 10 Wash with % ether / petroleum ether, remove the solvent, and recrystallize with 30 ml of hexane. Obtained compound 1.03 g (90.5% yield), melting point 195-198 ° C [a] 25D = -134.9, infrared [KBr, cm-1] 2958 (w), 2935 (m...

Embodiment 2

[0035] Under stirring, dissolve 2.00 g of racemic 1,1'-binaphthyl-2,2'-diphenol in 15 ml of 10% potassium hydroxide solution, cool to room temperature, and add 0.30 g of tetrabutyl Ammonium bromide and 15.0 milliliters of toluene were stirred rapidly, and 2.1 milliliters (80.9%, 1.4 equivalents) of menthyl chloroformate were added, and the reaction was kept at room temperature for 16 minutes, left to stand, and the organic layer was separated, and the aqueous layer was washed with dichloromethane 3×10 Extract in 1 ml, combine the organic layers, wash with 3×10 ml of water, dry over anhydrous sodium sulfate, filter, and remove the solvent by rotary evaporation to obtain a viscous liquid, recrystallize with 30 ml of petroleum ether at 60-90°C, concentrate the mother liquor, and pass through a short column , silica gel as the stationary phase, 5 cm long, 10% ether / petroleum ether rinse, remove the solvent, recrystallize with 30 milliliters of petroleum ether, combine the crystals,...

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Abstract

A preparation method of chiral binaphthalenediol, using L-(-)-menthol chloroformate as a resolving agent to generate diastereomeric derivatives, which are separated by recrystallization, and the derivatives are separated in water- Under the condition of alcohol or ketone, hydrolyze with strong base (NaOH, KOH), evaporate the organic solvent, extract with petroleum ether, neutralize the aqueous layer, extract with ether, dry, and remove the solvent to obtain the corresponding chiral binaphthol.

Description

technical field [0001] The invention relates to a preparation method of a class of optically active organic compounds, in particular to a preparation method of chiral binaphthyldiol. Background technique [0002] Optically pure 1,1'-binaphthyl and its analogs are important additives and catalyst ligands in asymmetric synthesis reactions, and are widely used in important organic synthesis reactions such as asymmetric cycloaddition, aldol condensation, and reduction . The preparation and application of such compounds has always been a very active research field in organic synthetic chemistry. [0003] The current means of resolving racemic 1,1'-binaphthol [602-09-5] and its derivatives include: [0004] 1) Utilize the functional group characteristics of BINOL to form diastereoisomers by forming esters, ethers or reacting with chiral amines, and achieve the purpose of resolution by means of crystallization. [0005] 2) Use the optically pure host compound and its enantiosele...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/225C07C37/68
Inventor 万伯顺李志安梁鑫淼吴凡
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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