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Preparation method of high-purity (±)-2,2'-bis-(2-hydroxyethoxy)-1,1'-binaphthyl

A hydroxyethoxylated, high-purity technology, applied in ether preparation, ester reaction to ether, organic chemistry, etc., can solve the problems of many side reactions, long reaction time, high reaction temperature, etc., to simplify post-processing steps and suppress side effects The formation of product polymers and the effect of improving production efficiency

Active Publication Date: 2020-06-26
JIANGSU EVER GALAXY CHEM CO LTD
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  • Abstract
  • Description
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Problems solved by technology

[0003] Documents J.Org.Chem.1977,42,4172-4182 and Helv.Chim.Acta1994,77(1),409-418 reported that binaphthol was reacted with ethyl chloroacetate and then reduced with lithium aluminum hydride to obtain (±)- 2,2'-di-(2-hydroxyethoxy)-1,1'-binaphthyl, the method has many steps, and the reducing agent lithium aluminum hydride used is flammable, explosive and unsafe, and must be prepared under absolutely anhydrous conditions next operation
Literature Org.BiomolecularChem.2012,10(47),9383-9392.; Tetrahedron,2013,69(49), 10662-10668.; Dyes and Pigments,2014,103,95-105. and Chinese patent CN1418878,2003 are all It is obtained by using chloroethanol as the hydroxyethylation reagent in the presence of alkalis such as sodium hydroxide or sodium carbonate, and reacting in solvents such as DMF or ethanol. The disadvantage of this method is that the reaction time is as long as 20-48 hours, and the chlorine used Ethanol is highly toxic
Japanese patent JP2011153248 uses ethylene carbonate as a hydroxyethylation reagent, in the presence of potassium hydroxide, at 170 o C reacts with (±)-1,1'-bi-(2-naphthol) to generate (±)-2,2'-di-(2-hydroxyethoxy)-1,1'-binaphthyl, which The reaction temperature of the method is high, the side reactions are many, and the color of the product is poor
Japanese patents JP201018753, JP2013227390 and JP 2014227387 also use ethylene carbonate as the hydroxyethylation reagent, sodium carbonate or potassium carbonate as the base, in toluene solvent at 110 o C makes (±)-1,1'-bi-(2-naphthol) hydroxyethylated. This method takes a long time to react and takes more than 10 hours, and a certain amount of polymer by-products are formed.

Method used

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  • Preparation method of high-purity (±)-2,2'-bis-(2-hydroxyethoxy)-1,1'-binaphthyl
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Embodiment 1

[0027] In a 500mL four-neck flask, add (±)-1,1'-bi(2-naphthol) 28.6g (0.1mol), 50g toluene, 4g N,N-dimethylacetamide, 1.9g potassium carbonate and Ethylene carbonate 22g (0.25mol). at 100 o C After 6 hours of reaction, the content of (±)-2,2'-bis-(2-hydroxyethoxy)-1,1'-binaphthyl was less than 0.1% by HPLC analysis, and the reaction was stopped. Add toluene, wash with water until neutral, cool to precipitate a solid, and vacuum dry for 12 hours to obtain (±)-2,2'-di-(2-hydroxyethoxy)-1,1'-binaphthalene 31.8g , the yield was 84.9%, the analytical purity by high performance liquid chromatography (HPLC) was 99.2%, and the melting endothermic peak range was 105-116 o C ( figure 1 ), the weight loss on drying at 120°C was 0.10%, and the TGA thermal analysis at 200°C lost 0.4% ( figure 2 ); 1 HNMR (CD 3 SOCD 3 ) δ: 3.86(t,4H), 4.03(t,4H), 6.90(d,2H), 7.23(d,2H), 7.34(dd,2H), 7.60(dd,2H), 7.92(d,2H ), 8.06 (d, 2H), 4.58 (s, 2H, plus D 2 O disappears).

Embodiment 2

[0029] In a 500mL four-neck flask, add (±)-1,1'-bi(2-naphthol) 28.6g (0.1mol), 50g toluene, 3g N,N-dimethylformamide, 1.9g potassium carbonate and Ethylene carbonate 22g (0.25mol). at 100 o C was reacted for 6 hours, and the content of (±)-1,1'-bi(2-naphthol) was less than 0.1% according to HPLC analysis, and the reaction was stopped. Add toluene, wash with water until neutral, cool to precipitate a solid, and vacuum dry for 12 hours to obtain (±)-2,2'-di-(2-hydroxyethoxy)-1,1'-binaphthalene 31.2g , the yield was 83.3%, the analytical purity by high performance liquid chromatography (HPLC) was 99.3%, and the melting endothermic peak range was 105-116 o C ( figure 1 ).

Embodiment 3

[0031] In a 1000mL four-neck flask, add (±)-1,1'-bi(2-naphthol) 114.4g (0.4mol), 100g toluene, 6gN,N-dimethylformamide, 7.5g potassium carbonate and carbonic acid Vinyl ester 88g (1mol). at 100 o C was reacted for 6 hours, and the content of (±)-1,1'-bi(2-naphthol) was less than 0.1% by HPLC analysis, and the reaction was stopped. Add toluene, wash with water until neutral, cool to precipitate a solid, and vacuum dry for 12 hours to obtain (±)-2,2'-di-(2-hydroxyethoxy)-1,1'-binaphthalene 125.8g , the yield was 84.1%, the analytical purity by high performance liquid chromatography (HPLC) was 99.3%, and the melting endothermic peak range was 105-116 o C ( figure 1 ), 120 o The loss on drying under C condition is 0.15%.

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Abstract

The invention provides a method for preparing a high-purity intermediate (+ / -)-2,2'-bi-(2-hydroxyethoxyl)-1,1'-dinaphthalene of a photoelectric material. According to the method provided by the invention, a polar aprotic solvent N,N-dimethyl acetamide or N,N-dimethyl formamide is adopted as a reaction promoter; a reaction time is shortened from 10 hours to approximately 6 hours; the production efficiency is greatly improved. Meanwhile, the formation of a by-product polymer is inhibited; a post treatment step is simplified.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a method for preparing a high-purity photoelectric material intermediate (±)-2,2'-bis-(2-hydroxyethoxy)-1,1'-binaphthyl. Background technique [0002] (±)-2,2'-di-(2-hydroxyethoxy)-1,1'-binaphthalene is an important intermediate of photoelectric materials, and the epoxy resin and acrylic resin derived from it have high refractive index , high thermal stability and good transparency and other excellent properties, it has important applications in light-emitting diode packaging materials, photoconductive devices, light-enhancing films, polarizing films, reflective films, optical lenses, gas separation films and electronic lithography materials. [0003] Documents J.Org.Chem.1977,42,4172-4182 and Helv.Chim.Acta1994,77(1),409-418 reported that binaphthol was reacted with ethyl chloroacetate and then reduced with lithium aluminum hydride to obtain (±)- 2,2'-di-(2-hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/16C07C43/23
CPCC07C41/16C07C43/23
Inventor 徐卫华苏波陆国元张强
Owner JIANGSU EVER GALAXY CHEM CO LTD
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