Preparation method of 3-site substituted benzoyl-beta-cyclodextrin

A technology of benzoyl and cyclodextrin, which is applied in the field of preparation of benzoyl-β-cyclodextrin, can solve the problems of many by-products and low yield, and achieve the effect of strong operability and selectivity

Active Publication Date: 2015-09-02
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method for preparing 2-substituted β-cyclodextrin derivatives is simple and convenient, there are many by-products and the yield is low.

Method used

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  • Preparation method of 3-site substituted benzoyl-beta-cyclodextrin
  • Preparation method of 3-site substituted benzoyl-beta-cyclodextrin
  • Preparation method of 3-site substituted benzoyl-beta-cyclodextrin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A preparation method of 3-substituted benzoyl-β-cyclodextrin, comprising steps as follows:

[0046] (1) Dissolve 6.63g (48mmol) of potassium carbonate and 6.81g (6.0mmol) of β-cyclodextrin in a mixed solvent consisting of 40mL of purified water and 15mL of N,N-dimethylformamide (DMF). solution;

[0047](2) Dissolve 6.75g (48mmol) of benzoyl chloride in 25mL of N,N-dimethylformamide (DMF), and add it dropwise to the mixed solution obtained in step (1) within 1h at 20°C, Add 3mol / L potassium hydroxide solution during the dropwise addition to maintain the pH of the solution between 9 and 11;

[0048] (3) After the dropwise addition is completed, neutralize the solution obtained in step (2) with 2mol / L hydrochloric acid to neutrality;

[0049] (4) Distill under reduced pressure at 75mmHg and 60°C, evaporate the solution obtained in step (3) to dryness, and vacuum-dry at 40°C for 6 hours to obtain a crude product;

[0050] (5) Add 10 g of the crude product obtained in ste...

Embodiment 2

[0062] A preparation method of 3-substituted benzoyl-β-cyclodextrin, comprising steps as follows:

[0063] (1) Dissolve 1g of potassium carbonate and 10g of β-cyclodextrin in a mixed solvent consisting of 20mL of N,N-dimethylformamide (DMF) and 50mL of purified water to obtain a mixed solution;

[0064] (2) Dissolve 10g of benzoyl chloride in 25mL of N,N-dimethylformamide (DMF), and add it dropwise to the mixed solution obtained in step (1) within 5 hours at 10°C. 3mol / L potassium hydroxide solution to maintain the pH of the solution between 9 and 11;

[0065] (3) After the dropwise addition is completed, neutralize the solution obtained in step (2) with 2mol / L hydrochloric acid to neutrality;

[0066] (4) Distill under reduced pressure at 75mmHg and 60°C, evaporate the solution obtained in step (3) to dryness, and vacuum-dry at 60°C for 4 hours to obtain a crude product;

[0067] (5) Add 15 g of the crude product obtained in step (4) into 50 mL of N,N-dimethylformamide (DMF...

Embodiment 3

[0071] A preparation method of 3-substituted benzoyl-β-cyclodextrin, comprising steps as follows:

[0072] (1) Dissolve 10 g of potassium carbonate and 1 g of β-cyclodextrin in a mixed solvent consisting of 20 mL of N,N-dimethylformamide (DMF) and 50 mL of purified water to obtain a mixed solution;

[0073] (2) Dissolve 10g of benzoyl chloride in 25mL of N,N-dimethylformamide (DMF), and add it dropwise to the mixed solution obtained in step (1) within 1 hour at 80°C. 3mol / L potassium hydroxide solution to maintain the pH of the solution between 9 and 11;

[0074] (3) After the dropwise addition is completed, neutralize the solution obtained in step (2) with 2mol / L hydrochloric acid to neutrality;

[0075] (4) Distill under reduced pressure at 75mmHg and 60°C, evaporate the solution obtained in step (3) to dryness, and vacuum-dry at 20°C for 6 hours to obtain a crude product;

[0076] (5) Add 6 g of the crude product obtained in step (4) into 50 mL of N,N-dimethylformamide (D...

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Abstract

The invention relates to a preparation method of 3-site substituted benzoyl-beta-cyclodextrin. The preparation method comprises the following steps: (1) adding potassium carbonate and beta-cyclodextrin into a DMF (dimethylfomamide) solution; (2) dissolving benzoyl chloride into DMF, dropwise adding the dissolved benzoyl chloride into the mixed solution obtained in the step (1), and maintaining the pH value of the solution to be 9-11; (3) after dropwise adding, neutralizing the solution obtained in the step (2) to be neutral; (4) performing reduced pressure distillation to dry the solution obtained in the step (3) by distillation, and drying to obtain a crude product; (5) adding the crude product into DMF, stirring uniformly, and performing reduced pressure suction filtration to obtain a filtrate; (6) concentrating the filtrate until the filtrate is saturated, dropwise adding acetone to obtain a deposit, and performing suction filtration to obtain 2-Bz-beta-CD; and (7) dissolving 2-Bz-beta-CD into a methanol solution, adding column chromatography silica gel, performing suction filtration, and drying the filtrate by distillation. According to the preparation method provided by the invention, a 2-substituted intermediate product is prepared firstly, and then a 3-substituted product is generated by virtue of 'self-transformation', so that the preparation method is economical, simple and convenient and is strong in selectivity.

Description

technical field [0001] The invention relates to a preparation method of 3-substituted benzoyl-β-cyclodextrin, which belongs to fine chemical industry. Background technique [0002] Cyclodextrin is an important host compound, which has an axisymmetric truncated cone-shaped cyclic oligosaccharide structure. According to the number of α-1,4-glucopyranose units (6,7,8) it contains The different corresponding names are α-, β-, γ-cyclodextrin. The cyclodextrin molecular cavity is hydrophobic (weak polarity), while the outer surface is hydrophilic (strong polarity). By modifying or preparing host-guest inclusion complexes, self-assembled bodies containing cyclodextrin structures have been applied in fields such as molecular recognition, drug delivery, gels, and microreactors. [0003] In the late 1990s, Bugler et al. and Ravoo et al. successively carried out hydrophobic modification on the main body of cyclodextrin, that is, introduced hydrophobic structural units (such as calixa...

Claims

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Application Information

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IPC IPC(8): C08B37/16
Inventor 鲁卓群郝爱友李啟谷锦阁
Owner SHANDONG UNIV
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