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Synthesis method of alkyl-substituted benzocrown ether

The technology of a benzocrown ether and a synthesis method, which is applied in the field of synthesizing crown ether compounds, can solve the problems of difficult control of reaction heat, poor reaction conversion rate, difficulty in separation and purification, etc., achieve complete conversion of raw materials, and avoid difficulty in feeding , The effect of simplifying the separation and purification process

Active Publication Date: 2014-01-01
TSINGHUA UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a synthetic method of alkyl-substituted benzocrown ethers, which solves the problem of poor reaction conversion rate, many side reactions, difficult separation and purification, and heat of reaction in the existing synthetic methods of alkyl-substituted benzocrown ethers. uncontrollable issues

Method used

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  • Synthesis method of alkyl-substituted benzocrown ether
  • Synthesis method of alkyl-substituted benzocrown ether
  • Synthesis method of alkyl-substituted benzocrown ether

Examples

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Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of C7 alkyl substituted dibenzo-18-crown-6

[0023] Using dibenzo-18-crown-6 and 2-methyl-2-hexanol as raw materials, the reaction equation for synthesizing C7 alkyl substituted dibenzo-18-crown-6 in dichloromethane solvent system is as follows:

[0024]

[0025] Dissolve 5.4g of dibenzo-18-crown-6 (DB18C6) in 75mL of dichloromethane, and then add 50g of polyphosphoric acid (PPA) to ensure that the system is fully stirred evenly. Dissolve 16g of 2-methyl-2-hexanol in 30mL of dichloromethane, and slowly drop the mixed solution into the aforementioned acidic solution system of DB18C6, and control the temperature of the system during the dropping process to not exceed 30°C. After the dropwise addition, keep stirring and react at 38°C for 3 hours

[0026] After the reaction, add deionized water to the system to hydrolyze PPA. The organic phase was separated and washed with water until neutral. Add anhydrous magnesium sulfate to the organic phase t...

Embodiment 2

[0027] Example 2: Synthesis of C6 alkyl substituted dibenzo-18-crown-6

[0028] Using dibenzo-18-crown-6 and 2-methyl-2-pentanol as raw materials, the reaction equation for synthesizing C6 alkyl substituted dibenzo-18-crown-6 in chloroform solvent system is as follows:

[0029]

[0030] Dissolve 5.4g of dibenzo-18-crown-6 (DB18C6) in 60mL of chloroform, and then add 40g of polyphosphoric acid (PPA) to ensure that the system is fully stirred evenly. Dissolve 15g of 2-methyl-2-pentanol in 20mL of chloroform, and slowly add the mixed solution dropwise into the aforementioned acidic solution system of DB18C6, and control the temperature of the system during the dropping process to not exceed 30°C. After the dropwise addition, keep stirring and react at 35°C for 4 hours

[0031] After the reaction, add deionized water to the system to hydrolyze PPA. The organic phase was separated and washed with water until neutral. Add anhydrous magnesium sulfate to the organic phase to dry...

Embodiment 3

[0032] Example 3: Synthesis of C5 alkyl substituted dibenzo-18-crown-6

[0033] Using dibenzo-18-crown-6 and tert-amyl alcohol as raw materials, the reaction equation for synthesizing C5 alkyl substituted dibenzo-18-crown-6 in toluene solvent system is as follows:

[0034]

[0035] Dissolve 5.4g of dibenzo-18-crown-6 (DB18C6) in 100mL of toluene, and then add 60g of polyphosphoric acid (PPA) to ensure that the system is fully stirred evenly. Dissolve 13.5g of tert-amyl alcohol in 30mL of toluene, and slowly drop the mixed solution into the aforementioned acidic solution system of DB18C6, and control the temperature of the system during the dropping process to not exceed 30°C. After the dropwise addition, keep stirring and react at 40° C. for 4 hours.

[0036] After the reaction, add deionized water to the system to hydrolyze PPA. The organic phase was separated and washed with water until neutral. Add anhydrous magnesium sulfate to the organic phase to dry, filter, and r...

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Abstract

The invention discloses a synthesis method of alkyl-substituted benzocrown ether, belonging to the technical field of synthesis of crown ether compounds. The synthesis process comprises the following steps of: dissolving a specific benzocrown ether raw material in an appropriate solvent system; and reacting with an alcohol compound which is dissolved in the specific solvent in advance, at lower reaction temperature under the catalytic action of polyphosphoric acid to obtain a corresponding alkyl-substituted benzocrown ether product. By adopting the synthesis process, the problems of low alkylation reaction transformation ratio of the conventional benzocrown ether and alcohol compound, the presence of side reaction, difficulty in separating and purifying, difficulty in controlling reaction heat and the like can be solved; the synthesis method is suitable for the synthesis and enlarged production of various types of alkyl-substituted benzocrown ethers; and the product is easy and convenient to purify, and has very high purity and the yield of over 90 percent.

Description

technical field [0001] The invention belongs to the technical field of synthesis of crown ether compounds, and in particular relates to a synthesis method of alkyl-substituted benzo crown ethers. Background technique [0002] In 1967, Pedersen synthesized and reported macrocyclic polyethers for the first time, which opened the prelude to the research on crown ethers (Pedersen et al. J. Am. Chem. S. 1967, 89, 7017-7036). The special property of crown ether lies in its strong ability to coordinate alkali metal and alkaline earth metal cations, and this coordination effect varies with the size of the hole in the ether ring, the type of heteroatom and the number of atoms. show a clear selectivity. As the subject compounds in many fields such as coordination chemistry, extraction chemistry, phase transfer catalysis, and ion-selective carriers, crown ethers have attracted more and more attention. In recent years, crown ether compounds have shown their application potential in th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D323/00
Inventor 叶钢高杰王建晨陈靖
Owner TSINGHUA UNIV
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