Preparations of 4-formyl biphenyl, 4-hydroxymethyl biphenyl and 4-chloromethyl biphenyl

A technology of formyl biphenyl and hydroxymethyl biphenyl is applied in the field of preparation of 4-formyl biphenyl, 4-hydroxymethyl biphenyl and 4-chloromethyl biphenyl, and can solve the problems affecting product purity, di The problems of mixing benzyl chloride and low yield, etc., achieve the effect of low production equipment requirements, easy control of conditions and strong price advantage

Active Publication Date: 2011-08-24
BEIJING ODYSSEY CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this method yield is not high, and benzyl chloride is mixed easily and influences product purity
[0008] Therefore, also lack a kind of preparation technology simple at present, cost is low, the synthetic method of 4 formyl biphenyl, 4 hydroxymethyl biphenyl and 4 chloromethyl biphenyl that recovery rate is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The preparation of embodiment 14 formyl biphenyl

[0051] 1. Weigh 300g of chlorobenzene, add 150g of anhydrous AlCl while stirring 3 , 10g CuCl and 100g biphenyl.

[0052] 2. After stirring for 30 minutes, heat up, and pass hydrogen chloride gas under the liquid surface at 30°C for 10 minutes. The weight of the hydrogen chloride gas passed is 2 g; The weight of carbon monoxide gas in the mixed gas is 60g, and the weight of hydrogen chloride gas in the mixed gas that passes through is 13g. When the gas chromatograph detects that the biphenyl content of the raw material is ≤1%, it is the end point of the reaction.

[0053] 3. Add 20 g of 35% hydrochloric acid and 600 g of crushed ice to the reaction product obtained in step 2 at a temperature of 0°C for thawing, keep the temperature at 0°C until the solids are completely dissolved, stir for 90 minutes, and let stand for 30 minutes After dividing the water layer; the organic phase is washed with 5% dilute hydrochloric ...

Embodiment 2

[0055] The preparation of embodiment 2 4-formylbiphenyl

[0056] 1. Weigh 2kg of chlorobenzene, add 1.2kg of anhydrous AlCl while stirring 3 , 0.1kg CuCl and 1kg biphenyl;

[0057] 2. After stirring evenly, under the condition of 36°C, first pass in hydrogen chloride gas for 10 minutes, and the weight of the hydrogen chloride gas is 1g; then pass in the mixed gas of carbon monoxide and hydrogen chloride for 24 hours, wherein, the mixed gas 90g of carbon monoxide gas, the weight of hydrogen chloride gas in the mixed gas introduced is 14g; gas chromatography detects that the raw material biphenyl content≤1% is the reaction end point.

[0058] 3. Add 0.12 kg of hydrochloric acid with a mass percentage concentration of 35% and 4 kg of crushed ice to the reaction product obtained in step 2 at a temperature of 5°C for thawing, keep the temperature at 10°C until the solids are completely dissolved, stir for 30 minutes, and let stand After 90 minutes, the water layer was separated; ...

Embodiment 3

[0060] Example 3 Preparation of 4-formylbiphenyl

[0061] 1. Weigh 5kg of chlorobenzene, add 1.5kg of anhydrous AlCl while stirring 3 , 0.2kg CuCl and 1kg biphenyl.

[0062] 2. Under the condition of 40°C, first pass hydrogen chloride gas for 50 minutes, wherein the weight of the hydrogen chloride gas passed is 30g; then pass the mixed gas of carbon monoxide and hydrogen chloride for 10 hours, the weight of carbon monoxide gas in the mixed gas passed is 600g, the weight of hydrogen chloride gas in the mixed gas that feeds is 150g, and gas chromatography detects that the raw material biphenyl content≤1% is the reaction end point.

[0063] 3. Add 1.2 kg of hydrochloric acid with a mass percentage concentration of 35% and 8 kg of crushed ice to the reaction product obtained in step 2 at 1 ° C for ice thawing, keep the temperature at 1 ° C until the solids are completely dissolved, stir for 60 minutes, and then divide after standing for 60 minutes Remove the water layer; the org...

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PUM

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Abstract

The invention relates to preparation methods of 4-formoxyl biphenyl, 4-hydroxymethyl biphenyl and 4-chloromethyl biphenyl, in particular to preparation methods which adopt biphenyl as substrate, anhydrous aluminum chloride and cuprous chloride as catalysts for preparing the 4-formoxyl biphenyl, and then use the 4-formoxyl biphenyl for preparing the 4-hydroxymethyl biphenyl and the 4-chloromethyl biphenyl. The methods have technical superiorities of high recovery ratio, simple reaction steps, easy-control conditions, applicability to industrialized production, low costs of raw materials, etc.

Description

technical field [0001] The present invention relates to a preparation method of 4-formyl biphenyl, 4-hydroxymethyl biphenyl and 4-chloromethyl biphenyl, in particular to a method using biphenyl as a substrate, anhydrous aluminum chloride, chloride A method for preparing 4-formyl biphenyl by using cuprous as a catalyst, and then using 4-formyl biphenyl to prepare 4-hydroxymethyl biphenyl and 4-chloromethyl biphenyl. Background technique [0002] 4-formyl biphenyl, 4-hydroxymethyl biphenyl, and biphenyl monochlorobenzyl are all important biphenyl derivatives, which are widely used in medicine, polymer liquid crystals, and dyes. For example, it can be used to synthesize non-steroidal anti-inflammatory drugs felbinac, fenbufen, anti-inflammatory analgesics ethyl felbinac, etc. [0003] At present, there have been many organic synthesis methods for the synthesis of 4-formylbiphenyl. Among them, U.S. Patent No. 5,068,450 adopts the reaction of formate ester in hydrofluoric acid-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/76C07C45/49
Inventor 吴细兵刘斌
Owner BEIJING ODYSSEY CHEM
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