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A method for preparing 3, 4-dihydroxy benzaldehyde in ionic liquid with one-pot method

A technology of dihydroxybenzaldehyde and p-hydroxybenzaldehyde is applied in the field of manufacture of dihydroxybenzaldehyde compounds, can solve the problems of long cyanide or process route, unfavorable industrialized production, and high raw material price, and achieves short process route and high production efficiency. Low cost and good selectivity

Inactive Publication Date: 2009-09-16
JIANGSU FOOD SCI COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Synthetic Chemistry), 2004, 12 (5): 484-486, 494. reported (preparation of high-purity 3,4-dihydroxybenzaldehyde), then prepared 3,4- Dihydroxybenzaldehyde, although there are few reaction steps and high yield, it uses toxic and harmful organic solvents methylene chloride and pyridine, and the price of raw materials is high
In addition, the synthesis process of o-bromophenol method and catechol method has also been developed, but the use of cyanide or long process route is not conducive to industrial production

Method used

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  • A method for preparing 3, 4-dihydroxy benzaldehyde in ionic liquid with one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Add 0.02mol of p-hydroxybenzaldehyde and 0.02mol of ionic liquid 1-butyl-3-methylimidazole tribromide to a three-necked flask, and carry out bromination reaction at 20°C for 30 minutes under stirring;

[0028] (2) 10mL of sodium hydroxide aqueous solution that sodium hydroxide and p-hydroxybenzaldehyde mol ratio are 1.25: 1 is added in the reaction solution that step (1) obtains, heat up to 100 ℃ under stirring state, and at this temperature Under hydrolysis reaction for 2 hours;

[0029] (3) The reaction solution obtained in step (2) was mixed with 0.1mol L -1 The hydrochloric acid solution was acidified to pH 5, then extracted with ethyl acetate, the extract was washed with saturated brine to pH 7, dried and evaporated to remove ethyl acetate, and the obtained substance was recrystallized with water to obtain 3,4-dihydroxybenzaldehyde white crystals.

[0030] (4) The remaining liquid after the extraction of step (3) was washed twice with 20mL ethyl acetate, and ...

Embodiment 2

[0033] (1) Add 0.02mol p-hydroxybenzaldehyde and 0.021mol ionic liquid 1-butyl-3-methylimidazole tribromide to a three-necked flask, and carry out bromination reaction at 25° C. for 25 minutes under stirring;

[0034] (2) 10mL of aqueous sodium hydroxide solution with a 1.5:1 mol ratio of sodium hydroxide and p-hydroxybenzaldehyde was added to the reaction solution obtained in step (1), heated to 120° C. under stirring, and at this temperature Lower hydrolysis reaction 1.5 hours;

[0035] (3) The reaction solution obtained in step (2) was mixed with 0.1mol L -1 The hydrochloric acid solution was acidified to pH 5, then extracted with ethyl acetate, the extract was washed with saturated brine to pH 7, dried and evaporated to remove ethyl acetate, and the obtained substance was recrystallized with water to obtain 3,4-dihydroxybenzaldehyde white crystals.

[0036] The obtained 3,4-dihydroxybenzaldehyde white crystals were 2.08 g, the yield was 75.2%, the melting point was 152-1...

Embodiment 3

[0039] (1) Add 0.02mol p-hydroxybenzaldehyde and 0.022mol ionic liquid 1-butyl-3-methylimidazole tribromide to a three-necked flask, and carry out bromination reaction at 15°C for 35 minutes under stirring;

[0040] (2) Add 10 mL of aqueous sodium hydroxide solution with a mol ratio of sodium hydroxide to p-hydroxybenzaldehyde of 1:1 to the reaction solution obtained in step (1), heat up to 80° C. under stirring, and Hydrolysis reaction for 2.5 hours;

[0041] (3) The reaction solution obtained in step (2) was mixed with 0.1mol L -1 The hydrochloric acid solution was acidified to pH 5, then extracted with ethyl acetate, the extract was washed with saturated brine to pH 7, dried and evaporated to remove ethyl acetate, and the obtained substance was recrystallized with water to obtain 3,4-dihydroxybenzaldehyde white crystals.

[0042] 1.81 g of white crystals of 3,4-dihydroxybenzaldehyde were obtained, the yield was 65.6%, the melting point was 152-153° C., and the purity was 99...

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Abstract

The present invention discloses a method for preparing 3, 4-dihydroxy benzaldehyde in ionic liquid with one-pot method, comprising the following steps: (1) adding p-hydroxybenzaldehyde and ionic liquid into a container in the proportion of mol as 1:1 to 1.3, and undergoing 20 to 40 minutes of brominating reaction in churning with a temperature of 10 DEG C to 30 DEG C; (2) in the reaction solution of the step (1), adding alkaline solution in a proportion of mol as 1 to 2:1 with p-hydroxybenzaldehyde, heating the solution to the temperature of 60 to 120 DEG C in churning, and undergoing 1 to 2.5 hours of hydrolysis in the temperature; and (3) acidifying the acquired reaction solution with hydrochloric acid solution to a pH value of 4.5 to 5.5, after extraction with organic solvent, washing the organic solvent with saturated salt water to a pH value of 6.5 to 7, removing the organic solvent after drying, re-crystallizing the generated material with water to acquire white crystal of 3, 4-dihydroxy benzaldehyde. The present invention has the advantages of short processing route, moderate reaction condition, good selectivity, high yield, low production cost and no environment pollution in production procedure.

Description

Technical field: [0001] The invention relates to a method for manufacturing dihydroxybenzaldehyde compounds, belonging to the field of chemical manufacturing technology. Background technique: [0002] 3,4-Dihydroxybenzaldehyde is an important organic synthesis raw material and pharmaceutical intermediate, which can be used to synthesize a variety of antibiotics and anti-inflammatory drugs, such as the synthesis of 3,4-dihydroxybenzaldehyde with biological activities such as antibacterial, antiviral and anticancer Hydroxybenzaldehyde semicarbazone; Synthesis of Danshensu, which has the functions of dilating blood vessels and increasing coronary blood flow, etc.; Coordination with germanium to synthesize organic compounds that have anti-cancer, anti-aging, antibacterial, anti-inflammatory, nutritional and health effects in medicine. Germanium; as the main component of Danshen injection, it has the effects of dilating blood vessels, improving microcirculation, protecting the li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/565C07C45/64
Inventor 刘长春
Owner JIANGSU FOOD SCI COLLEGE
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