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Method for preparing 2,4-dihydroxy benzaldehyde

A technology of dihydroxybenzaldehyde and dimethylformamide is applied in the field of preparation of 2,4-dihydroxybenzaldehyde, which can solve the problems of dangerous use, transportation and storage, environmental pollution, corrosion of equipment, etc., so as to reduce resource consumption, The reaction process is safe and the effect of less environmental pollution

Inactive Publication Date: 2017-09-15
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These halogenated reagents are toxic and corrosive and absorb moisture when exposed to air
Phosphorus trichloride and thionyl chloride will also produce a series of waste liquid and waste gas such as phosphoric acid and sulfur dioxide during use, which will corrode equipment and pollute the environment
However, phosgene is a highly toxic gas, which is very dangerous during use, transportation and storage.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Under ice-salt bath, stir and mix 1.39 g (4.68 mmol) BTC and 10 mL chloroform. When the temperature is kept at -5°C, add 3 mL (38.99 mmol) DMF dropwise within 30 min, and bubbles overflow through the tail gas absorption device The rate controls the rate of addition; after all the DMF has been added dropwise, continue to stir for 20 min in an ice-salt bath at -5°C, add 1.11 g (10.08 mmol) of resorcinol, heat to 30°C, monitor the reaction process by TLC, and react for 5 hours. Part of the solvent was evaporated, cooled, filtered with suction, recrystallized with water, and the yield was 72.46%. Melting point: 136-138°C.

Embodiment 2

[0020] Under ice-salt bath, 1.39 g (4.68 mmol) of BTC and 10 mL of 1,2-dichloroethane were stirred and mixed. When the temperature was kept at -5°C, 3 mL (38.99 mmol) of DMF was added dropwise within 30 min. The drop rate is controlled by the bubble overflow rate of the tail gas absorption device; after all the DMF is added dropwise, continue to stir for 10 min in an ice-salt bath at -5°C, add 1.11 g (10.08 mmol) resorcinol, heat to 40°C, and monitor the reaction process by TLC , reacted for 5 hours, distilled off part of the solvent, cooled, filtered with suction, recrystallized from water, and the yield was 64.46%.

Embodiment 3

[0022] Under ice-salt bath, stir and mix 1.39 g (4.68 mmol) BTC and 10 mL dichloromethane. When the temperature is kept at 5°C, add 3 mL (38.99 mmol) DMF dropwise within 22 min. Control the rate of addition; after all the DMF has been added dropwise, continue to stir in an ice-salt bath at 0°C for 30 min, add 1.11 g (10.08 mmol) of resorcinol, heat to 45°C, monitor the reaction process by TLC, react for 5 hours, and evaporate Part of the solvent, cooling, suction filtration, water recrystallization, yield 68.13%.

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Abstract

The invention relates to a method for preparing 2,4-dihydroxy benzaldehyde. The method comprises the following steps: by taking m-dihydroxybenzene as a raw material, performing reaction on bis(trichloromethyl) carbonate triphosgene BTC and N,N-dimethylformamide DMF in an organic solvent, and purifying, thereby obtaining a target compound. According to the method, as the triphosgene is adopted to replace a phosphorus-containing or sulfur-containing chlorination agent, the problems of treatment of a great amount of phosphorus-containing or sulfur-containing byproducts, discharging of wastewater and the like in the production process are solved, and the method has the characteristics of being easy in raw material obtaining, gentle in reaction condition, simple in operation step, low in cost, low in energy consumption, small in pollution, possible in clean production and the like and has industrial application prospects.

Description

technical field [0001] The present invention relates to a new method for preparing 2,4-dihydroxybenzaldehyde, in particular to the preparation of 2,4- Dihydroxybenzaldehyde belongs to the field of chemical preparation technology. Background technique [0002] 2,4-Dihydroxybenzaldehyde, as an aromatic aldehyde, is widely used in dyes, medicines, pesticides, spices, materials and other fields. There are hydroxyl and aldehyde active functional groups in its structure, which can be easily converted into other compounds. As an important class of fine chemical raw materials, it is widely used in organic synthesis, chemical analysis, coordination chemistry, chemical additives, drugs, pesticides, dyes, luminescent materials, Photosensitive materials and other aspects have greater application value and significance. [0003] At present, the reported synthesis methods of 2,4-dihydroxybenzaldehyde mainly include: Reimer-Tiemann synthesis method, Gattermann-Koch reaction, Friedel-Craf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C45/54C07C47/565C07C68/00C07C69/96
CPCC07C45/00C07C45/54C07C68/00
Inventor 但飞君孙铭皓郑星星刘康辉
Owner CHINA THREE GORGES UNIV
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