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One-pot technology of 4'-methyl-2-carboxylate biphenyl

The technology of ester biphenyl and cyano biphenyl is applied in the field of 4'-methyl-2-carboxylate biphenyl one-pot process, which can solve the problems of high labor intensity, long time consumption, environmental pollution of material circulation, etc.

Inactive Publication Date: 2015-11-25
SHANDONG FANGMING PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1. The intermediate product 4′-methyl-2-carboxylic acid biphenyl must be separated before the next step of esterification;
[0006] 2. During the separation process, there is a risk of environmental pollution caused by material circulation and leakage;
[0007] 3. It is necessary to increase the separation equipment, and the labor intensity of the workers is high;
[0009] 5. The hydrolysis of 4′-methyl-2-cyanobiphenyl needs more than 48 hours to complete the hydrolysis, which takes a long time;

Method used

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  • One-pot technology of 4'-methyl-2-carboxylate biphenyl
  • One-pot technology of 4'-methyl-2-carboxylate biphenyl

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Example 1. Install a reflux condenser with condensed water at or below normal temperature on the 250ml four-neck flask with electric PTFE stirring, a thermometer at 0-200°C, and a matching adjustable constant temperature electric heating oil bath or adjustable Constant temperature electric heating mantle and other heating devices. Add 12.5 grams of 4'-methyl-2-cyanobiphenyl and 30 grams of 30% dilute sulfuric acid into a four-necked flask, heat, and reflux at a temperature of 106 to 113°C for 24 hours; then cool down and add toluene (content 99%) 20 grams, install a 10ml water separator with a scale, heat and reflux to divide the water until about 18.5ml of water is separated, stop heating and cool down, and release the water layer in the water separator; when the temperature drops to normal temperature, Add 5 grams of methanol, heat and continue to reflux, react for 8 hours, and steam the remaining methanol. At this time, the reflux temperature will reach 115° C., end...

Embodiment 2

[0017] Example 2. On the 250ml four-necked flask with electric PTFE stirring, install a reflux condenser with condensed water at or below normal temperature, a thermometer at 0-200°C, and a matching adjustable constant temperature electric heating oil bath or adjustable Constant temperature electric heating mantle and other heating devices. Add 12.5 grams of 4′-methyl-2-cyanobiphenyl, 15 grams of 60% dilute sulfuric acid and 20 grams of toluene (content 99%) into a four-neck flask, heat, and reflux at a temperature of 110 to 115 ° C for hydrolysis reaction 24 hours; then lower the temperature, install a 10ml water separator with a scale, heat and reflux to divide the water until about 3.5ml of water is separated, stop heating and cool down, and release the water layer in the water separator; when the temperature drops to normal temperature, Add 5 grams of methanol, heat and continue to reflux, react for 8 hours, and steam the remaining methanol. At this time, the reflux tempe...

Embodiment 3

[0019] Example 3. On the 250ml four-necked flask with electric PTFE stirring, install a reflux condenser with condensed water at or below normal temperature, a thermometer at 0-200°C, and a matching adjustable constant temperature electric heating oil bath or adjustable Constant temperature electric heating mantle and other heating devices. Add 12.5 grams of 4′-methyl-2-cyanobiphenyl, 12 grams of 75% dilute sulfuric acid and 20 grams of toluene (content 99%) into a four-neck flask, heat, and reflux at a temperature of 110 to 115 ° C for hydrolysis reaction 24 hours; then lower the temperature, install a 10ml water separator with a scale, heat and reflux to divide the water until about 0.5ml of water is separated, stop heating and cool down, and release the water layer in the water separator; when the temperature drops to normal temperature, Add 5 grams of methanol, heat and continue to reflux, react for 8 hours, and steam the remaining methanol. At this time, the reflux tempe...

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Abstract

The invention discloses a one-pot technology of 4'-methyl-2-carboxylate biphenyl. In a same reaction container, under the acidic condition, 4'-methyl-2-cyanobiphenyl is hydrolyzed within 24 h to generate 4'-methyl-2-biphenyl carboxylate; an organic solvent which is hard to dissolve in water is then used to carry out refluxing so as to remove superfluous water; organic compounds containing hydroxyl groups such as alcohol and the like are added; and under the catalysis of an esterification catalyst such as sulfuric acid and the like, 4'-methyl-2-carboxylate biphenyl is generated. Multiple flowing of materials is avoided, generation of ammonia gas and salt-containing wastewater is avoided, and environmental friendliness is increased. Investment in ammonia gas absorption and intermediate product separation equipment is minimized, synthesis period is short, manpower and material resources are saved, and costs are reduced. A by-product ammonium sulfate can be used as a raw material of an agricultural compound fertilizer, thus achieving the purpose of comprehensive utilization.

Description

technical field [0001] The invention relates to a 4'-methyl-2-carboxylate biphenyl one-pot process, which belongs to the technical field of chemical synthesis. Background technique [0002] 4′-Methyl-2-carboxylate biphenyl is an important intermediate of the sartan antihypertensive drug Telmisartan. The existing production process uses 4′-methyl-2-cyanobiphenyl as raw material. Alkaline hydrolysis, acidification, and esterification to synthesize 4'-methyl-2-carboxylate biphenyl. The reaction principle is as follows: [0003] [0004] This route has the following problems: [0005] 1. The intermediate product 4′-methyl-2-carboxylic acid biphenyl must be separated before the next step of esterification; [0006] 2. During the separation process, there is a risk of environmental pollution caused by material circulation and leakage; [0007] 3. It is necessary to increase the separation equipment, and the labor intensity of the workers is high; [0008] 4. The generated ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/767C07C67/08
Inventor 张立余洪智范兴山
Owner SHANDONG FANGMING PHARMACEUTICAL CO LTD
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