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Method for preparing p-hydroxybenzene methanal with Reimer-Tiemann reaction

A p-hydroxybenzaldehyde, reaction technology, applied in the field of preparation of p-hydroxybenzaldehyde, can solve the problems of non-reusable, difficult industrial application, expensive catalyst, etc., and achieve the effect of being beneficial to industrial production, low cost, and easy to control the reaction

Inactive Publication Date: 2008-09-24
山东兴安智慧科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these catalysts are expensive and cannot be reused, making them difficult to apply industrially.

Method used

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  • Method for preparing p-hydroxybenzene methanal with Reimer-Tiemann reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 4.7g of phenol, 10g of sodium hydroxide, 20g of water, 10g of methanol, and 0.5g of 201×4 resin (Shanghai Hualing Resin Co., Ltd.) into the three-necked flask, stir vigorously, heat the oil bath to 40°C, and add 20 g of chloroform was added dropwise, and the reaction temperature was maintained for 3 hours. After reaction finishes, suction filtration reclaims catalyzer, and dilute hydrochloric acid (18%, w / w) regulates the pH value of filtrate to 6, steam distillation until no oil droplet steams out, and a small amount of o-hydroxybenzaldehyde and chloroform are steamed out, Add 10 mL of dichloromethane to the distillate, extract, separate layers, and rotary evaporate to obtain 0.18 g of o-hydroxybenzaldehyde with a yield of 3%. The purity measured by gas chromatography is 99.5%. The residual liquid obtained after steam distillation was frozen and filtered with suction to obtain crude p-hydroxybenzaldehyde, which was recrystallized with 50% (v / v) ethanol aqueous solu...

Embodiment 2

[0030] Add 4.7g of phenol, 25g of sodium hydroxide, 20g of water, 10g of ethanol, 0.5g of D201 resin (Anhui Wandong Chemical Co., Ltd.) into the three-necked flask, stir vigorously, heat the oil bath to 40°C, and dropwise Chloroform 20g, keep reaction temperature 3 hours. After reaction finishes, suction filtration reclaims catalyzer, and dilute hydrochloric acid (18%, w / w) regulates the pH value of filtrate to 6, steam distillation until no oil droplet steams out, and a small amount of o-hydroxybenzaldehyde and chloroform are steamed out, Add 10 mL of dichloromethane to the distillate, extract, separate layers, and rotary evaporate to obtain 0.21 g of o-hydroxybenzaldehyde with a yield of 3.4%. The purity measured by gas chromatography is 99.5%. The product liquid obtained by steam distillation was frozen, filtered with suction to obtain the crude product of p-hydroxybenzaldehyde, which was recrystallized with 50% (v / v) ethanol aqueous solution to obtain 4.1 g of needle-like ...

Embodiment 3

[0032]Add 4.7g of phenol, 40g of sodium hydroxide, 40g of water, 20g of benzene, and 0.5g of 201×7 resin (Bengbu Liaoyuan New Material Co., Ltd.) in the three-necked flask, stir vigorously, heat the oil bath to 40°C, and add to the reaction solution Chloroform 20g was added dropwise in the solution, and the reaction temperature was maintained for 3 hours. After reaction finishes, suction filtration reclaims catalyzer, and dilute hydrochloric acid (18%, w / w) regulates the pH value of filtrate to 6, steam distillation until no oil droplet steams out, and a small amount of o-hydroxybenzaldehyde and chloroform are steamed out, Add 10 mL of dichloromethane to the distillate, extract, separate layers, and rotary evaporate to obtain 0.20 g of o-hydroxybenzaldehyde with a yield of 3.4%. The purity measured by gas chromatography is 99.5%. The product liquid obtained by steam distillation was frozen and filtered with suction to obtain crude p-hydroxybenzaldehyde, which was recrystallize...

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Abstract

The present invention provides a method used for preparing p-hydroxybenzaldehyde through Reimer-Tiemann reaction. In the method, phenol, chloroform, alkali and a phase-transfer catalyst react in a reaction medium to prepare the p-hydroxybenzaldehyde. The reaction medium can be one of water, methanol aqueous solution, ethanol aqueous solution, glycerin aqueous solution, benzene aqueous solution and toluene aqueous solution. The phase-transfer catalyst can be one of 201*4 resin, 201*7 resin, D301 Resin and D201 resin. The method has the following beneficial effects: (1) the cheap and easily prepared methanol aqueous solution, ethanol, glycerin and so on are used as the reaction solvent, which facilitates the heterogeneous reaction and the industrial production; (2) the D301 Resin, D201 resin and so on are used as the catalyst; thus the reaction can be easily controlled; the reaction yield is high; the catalyst can be recycled and reused; the cost is low; and the method facilitates the industrial production.

Description

(1) Technical field [0001] The invention relates to a method for preparing p-hydroxybenzaldehyde, in particular to a method for preparing p-hydroxybenzaldehyde by Reimer-Tiemann reaction. (2) Background technology [0002] 4-Hydroxybenzaldehyde is a very important intermediate in organic synthesis. It is widely used in medicine, spices, pesticides, petrochemicals, electroplating, liquid crystal and other fields because of its very active hydroxyl and aldehyde groups in its molecules. With the domestic and foreign markets increasing demand for antibacterial synergist methoxypyrimidine (TMP), new heart disease drugs p-hydroxyphenylacetamide, hydroxyphenylglycine and other pharmaceutical products and spices, the demand for p-hydroxybenzaldehyde Synthesis is once again receiving a lot of attention. [0003] There are many industrial preparation methods of p-hydroxybenzaldehyde, such as Reimer-Tiemann method, p-nitrotoluene method, p-chlorophenol method, p-cresol catalytic oxida...

Claims

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Application Information

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IPC IPC(8): C07C47/565C07C45/43B01J31/06
CPCY02P20/584
Inventor 裴文陶金海张秀花
Owner 山东兴安智慧科技有限公司
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