Synthetic method of diol phenylate compounds

A synthetic method, a technology of diol phenyl ether, applied in the preparation of organic compounds, chemical instruments and methods, the formation/introduction of ether groups/acetal groups/ketal groups, etc., can solve the problem of corrosiveness and low yield of products , dangerous epoxy compounds and other issues, to achieve the effect of non-corrosive preparation and convenient use

Inactive Publication Date: 2012-08-01
CHANGZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the existing synthesis method of ethylene glycol phenyl ether compounds, phenol and oxirane are used for synthesis, but this type of method will use dangerous epoxy compounds, and the catalyst used is expensive and corrosive, and the obtained The product is low yield and the product is complex
Anil K.Kinage and others have improved the synthetic method of diol phenyl ethers. They use phenol and cyclocarbonate to react in KL molecular sieves, but this method needs to be carried out at a higher temperature, and the catalyst is difficult to prepare, and This reaction will produce 2-(2-phenoxyethoxy)ethanol by-products

Method used

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  • Synthetic method of diol phenylate compounds
  • Synthetic method of diol phenylate compounds
  • Synthetic method of diol phenylate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of glycol phenyl ether compounds shown in embodiment 1, formula (II)

[0021]

[0022] Put 0.102g of iodobenzene (0.5mmol), 0.0095g of cuprous iodide (0.05mmol), and 0.276g of potassium carbonate (2mmol) into a 50ml reaction vessel dried in an oven, and inject 0.248g of ethylene di Alcohol (4mmol), 2ml toluene, in this reaction system, the mol ratio of iodobenzene and glycol is 1: 8, and the mol ratio of iodobenzene and potassium carbonate is 1: 4, and cuprous iodide accounts for the molar percentage of iodobenzene The content was 10%, reacted for 24 hours, extracted with ethyl acetate and concentrated with a rotary evaporator and passed through the column (ethyl acetate:petroleum ether=4:1, v / v) to obtain 28.4mg of product with a yield of 41.2%IR (film )vmax3391, 3063, 3040, 2932, 2876, 1599, 1495, 1455, 1246; 1 H NMR (500MHz, CDCl 3 )δ2.05(s, 1H3.97(t, J=4.0Hz, 2H), 4.09(t, J=4.0Hz, 2H), 6.92-6.99(m, 3H), 7.29(d, J=12Hz, 2H); 13 C NMR (500MHz, CDCl 3...

Embodiment 2

[0023] Synthesis of glycol phenyl ether compounds shown in embodiment 2, formula (II)

[0024] With 0.102g iodobenzene (0.5mmol), inject 0.031g ethylene glycol (0.5mmol), 2ml toluene, in this reaction system, the molar ratio of iodobenzene and diol is 1: 1, other conditions are as embodiment 1, obtain 6.9mg product, yield 10%

Embodiment 3

[0025] Synthesis of diol phenyl ether compounds shown in embodiment 3, formula (II)

[0026] With 0.102g iodobenzene (0.5mmol), inject 0.124 ethylene glycol (2mmol), 2ml toluene, in this reaction system, the molar ratio of iodobenzene and diol is 1: 4, other conditions are as embodiment 1, obtain 18.63mg product, yield 27%

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Abstract

The invention relates to a synthetic method of diol phenylate compounds, which is characterized in that raw material comprises aromatic compounds, diol, metal salt catalysts, alkali, reaction promoting ligand and reaction solvent; the raw material is added in a reactor and stirred for 1 to 72 hours under the temperature ranging from 50 to 220 DEG C; the raw material is extracted through organic solvent and concentrated through a rotary evaporator, and then the diol phenylate compounds are obtained through column passing; a chemical reaction equation is shown in a patent specification; the synthetic method achieves high efficiency; in addition, metal salt is adopted as the catalysts, so that non-corrosiveness can be achieved, and the synthetic method is convenient to prepare and use.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of diol phenyl ether compounds. Background technique [0002] Glycol phenyl ether series are widely used in automobile and automobile repair coatings, electrophoretic coatings, industrial baking varnishes and ships because of their non-toxicity, good miscibility, moderate volatilization rate, excellent coalescence and coupling ability, and low surface tension. Containers, wood coatings. It is a good solvent for polymers such as oils / natural resins / cellulose fibers / alkyd resins. Widely used as solvents and specialty chemicals for personal care products such as soaps, detergents, perfumes, cosmetics, toilet products and the pharmaceutical industry. [0003] In the existing synthesis method of ethylene glycol phenyl ether compounds, phenol and oxirane are used for synthesis, but this type of method will use dangerous epoxy compound...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/04C07C41/16C07C43/23C07C205/37C07C201/12C07D213/69
Inventor 王治明李申王钰蓉于斌孙小强李小明
Owner CHANGZHOU UNIV
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