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Phenolic compound synthesizing method taking water as solvent

A technology of phenolic compounds and synthesis methods, which is applied in the field of synthesis and preparation of chemical products, can solve problems such as pollution and high yields, and achieve the effects of cheap and easy-to-obtain reaction raw materials, high yields, and low environmental pollution

Inactive Publication Date: 2010-07-14
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] These existing conventional synthesis methods of phenolic compounds not only need organic solvents as solvents and noble metals as catalysts, but also usually require harsh reaction conditions (high temperature and high pressure), and can achieve relatively high efficiency under the premise of producing a lot of pollution to the environment. Yield of

Method used

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  • Phenolic compound synthesizing method taking water as solvent
  • Phenolic compound synthesizing method taking water as solvent
  • Phenolic compound synthesizing method taking water as solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Add 7 mg of cuprous oxide, 120 mg of sodium hydroxide, 12 mg of 2-pyridine formaldehyde oxime, 65 mg of tetra-n-butylammonium bromide and 201 mg of o-bromobenzoic acid into a Schrank test tube equipped with a magnetic stirring bar. After the Schrank test tube was evacuated twice, it was filled with nitrogen, and 1 mL of water was added to the Schrank test tube at room temperature, then the Schrank test tube was sealed and placed in an oil bath at 100°C under nitrogen atmosphere. Under pressure, react for 48 hours. After the reaction was completed, cool to room temperature, then add 2 mL of 1 mol / L hydrochloric acid for acidification (pH 2-3), extract 3 times with ethyl acetate, 2 mL each time, the combined organic phase was concentrated, and the residue Purification was carried out through a silica gel column to obtain 124 mg of o-hydroxybenzoic acid with a yield of 90%.

[0057] Product o-hydroxybenzoic acid: 1 H NMR (DMSO-d 6 , 300MHz, ppm) δ11.8(s, br, 1H), 7.79(d...

Embodiment 2

[0059] 19 mg of cuprous iodide, 168 mg of potassium hydroxide, 12 mg of 2-pyridine formaldehyde oxime, 65 mg of tetra-n-butylammonium bromide and 239 mg of 1-chloro-4-iodobenzene were added to a Schrank test tube equipped with a magnetic stirring bar. After the Schrank test tube was evacuated twice, it was filled with nitrogen, and 1 mL of water was added to the Schrank test tube at room temperature. Under pressure, react for 48 hours. After the reaction was completed, cool to room temperature, then add 2 mL of 1 mol / L hydrochloric acid for acidification (pH 2-3), extract 3 times with ethyl acetate, 2 mL each time, the combined organic phase was concentrated, and the residue Purification was carried out through a silica gel column to obtain 78 mg of 4-chlorophenol with a yield of 61%.

[0060] Product 4-chlorophenol: 1 H NMR (CDCl 3 , 300MHz, ppm) δ7.19(d, 2H, J=7.9Hz), 6.77(d, 2H, J=7.9Hz), 5.13(s, br, 1H). 13 C NMR (CDCl 3 , 75MHz, ppm) δ154.1, 129.6, 125.8, 116.8.ESI-M...

Embodiment 3

[0062] 19 mg of cuprous iodide, 450 mg of cesium hydroxide, 12 mg of 2-pyridine formaldehyde oxime, 65 mg of tetra-n-butylammonium bromide and 239 mg of 1-chloro-4-iodobenzene were added to a Schrank test tube equipped with a magnetic stirring bar. After the Schrank test tube was evacuated twice, it was filled with nitrogen, and 1 mL of water was added to the Schrank test tube at room temperature. Under pressure, react for 48 hours. After the reaction was completed, cool to room temperature, then add 2 mL of 1 mol / L hydrochloric acid to acidify (pH 2-3), extract 3 times with ethyl acetate, 2 mL each time, the combined organic phase was concentrated, and the residue Purification was carried out through a silica gel column to obtain 85 mg of 4-chlorophenol with a yield of 66%.

[0063] Product 4-chlorophenol: 1 H NMR (CDCl 3 , 300MHz, ppm) δ7.19(d, 2H, J=7.9Hz), 6.77(d, 2H, J=7.9Hz), 5.13(s, br, 1H). 13 C NMR (CDCl 3 , 75MHz, ppm) δ154.1, 129.6, 125.8, 116.8.ESI-MS[M-H] - ...

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Abstract

The invention relates to a phenolic compound synthesizing method taking water as a solvent. Under a mild reaction condition, the method takes aryl halides as the raw material, takes water as the solvent, takes alkali metal hydroxides (including sodium, potassium, cesium and the like) as alkalis, takes cuprous oxide, cuprous iodide, cuprous bromide or cuprous chloride as the catalyst, takes 2-pyridine formaldoxime as a ligand and takes 4-n-butyl ammonium bromide as the phase transfer catalyst, the reaction temperature is about 100-110 DEG C, and then phenolic compound is efficiently synthesized. Compared with the conventional phenolic synthesis method, the method takes the cheap and easily obtained aryl halides as the raw materials, takes the cheapest water as the solvent and takes the cheap cuprous oxide as the catalyst, the reaction condition is mild, the environmental pollution is small, the yield of generated phenol is high, the tolerance on various functional groups on an aromatic ring is high, separation and purification are convenient and the like, and the method can be widely applied in synthesis in the fields of medicines, polymers, natural products and the like of industrial community and academia.

Description

technical field [0001] The present invention generally relates to the synthesis and preparation of a class of chemical products, and more specifically relates to the synthesis method of phenolic compounds. Background technique [0002] Phenolic compounds are important chemical raw materials and intermediates. Taking the most common phenol as an example, phenol can be used as a fungicide, anesthetic, and preservative. Joseph Lister (Lister J) first used it for surgical disinfection. Now phenol can be used to prepare disinfectants, and its dilute solution can be used for direct disinfection. Phenol is mainly used in the manufacture of phenolic resins, bisphenol A and caprolactam. Alkylphenols produced from phenol are monomers for preparing alkylphenol-formaldehyde polymers, and can be used as antioxidants, nonionic surfactants, plasticizers, and petroleum product additives. Phenol is also a raw material for many medicines (such as salicylic acid, aspirin and sulfa drugs, e...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C37/02C07C39/28C07C39/04C07C39/06C07C39/27C07C39/38C07C51/367C07C65/10C07C65/03C07C201/12C07C205/22C07C205/60C07C47/565C07C45/64C07C213/00C07C215/76C07C233/75C07C231/12C07D213/80C07D213/803
CPCY02P20/52
Inventor 付华杨道山杨海军
Owner TSINGHUA UNIV
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