Method for preparing aryl propanal derivatives

A technology for aryl propionaldehyde and derivatives, which is applied in the field of preparation of aryl propionaldehyde derivatives, can solve the problems of harsh reaction conditions, high production equipment requirements, high pressure on safety and environmental protection, etc., and achieves easy industrial production and production equipment requirements. Low, three-waste emissions are small

Inactive Publication Date: 2011-05-18
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the need to use the precious metal palladium and the production of isomers, the method is limited in application
[0012] Looking at the preparation methods of arylpropionaldehyde derivatives that have been disclosed, the sources of raw materials are difficult and expensive, and multiple oxidation and reduction reactions or the use of noble metal palladium or noble metal nickel are required. The route is lengthy, the reaction conditions are harsh, and the operability is poor. Production equipment High requirements, high pressure on safety and environmental protection, difficult product purification, low yield, unfavorable for industrial production

Method used

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  • Method for preparing aryl propanal derivatives
  • Method for preparing aryl propanal derivatives
  • Method for preparing aryl propanal derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the preparation of m-trifluoromethyl phenylpropanal

[0044] Preparation of 1-(3-ethoxyallyl)-3-(trifluoromethyl)benzene

[0045] Under nitrogen, m-trifluoromethylbromobenzene (23 g, 0.1 mol), magnesium (29 g, 1.2 mol), 60 ml of ether and 50 mg of iodine were added to the reaction flask, heated to initiate the reaction, and then m-trifluoromethyl Bromobenzene (230 g, 1 mole) and 360 ml of diethyl ether were dropped into the reaction flask and kept boiling slightly. After dropping, the mixture was stirred and reacted at reflux for 2 hours. After the reaction was completed, it was cooled to room temperature, and acrolein diethyl acetal (14.3 g, 0.11 mol) and cuprous iodide (1.9 g, 0.01 mol) were added. The reaction was stirred at reflux for 12 hours. After the reaction, the pH value was adjusted to 7 with saturated ammonium chloride aqueous solution at 0°C. Diethyl ether was distilled off, 50 ml of ethyl acetate was added, the organic layer was separated...

Embodiment 2

[0057] Embodiment 2: the preparation of p-tert-butylphenylpropionaldehyde

[0058] Preparation of 1-tert-butyl-4-(3-ethoxyallyl)benzene

[0059] Under nitrogen, p-tert-butylbromobenzene (2.1 g, 0.01 mole), magnesium (4 g, 0.17 mole), 10 milliliters of tetrahydrofuran and 50 mg of iodine were added to the reaction flask, heated to initiate the reaction, and p-tert-butylbromobenzene (21.3 g, 0.1 mol) and 60 ml of tetrahydrofuran were dropped into the reaction flask. After dropping, the reaction was stirred at -20°C for 72 hours. After the reaction was completed, it was cooled to room temperature, acrolein diethyl acetal (13 g, 0.1 mol) and cuprous bromide (0.7 g, 0.005 mol) were added, and the reaction was stirred at -20°C for 72 hours. After the reaction, the pH value was adjusted to 7 with saturated ammonium chloride aqueous solution at 0°C. The tetrahydrofuran was distilled off, 50 ml of ethyl acetate was added, the organic layer was separated, and the aqueous layer was ex...

Embodiment 3

[0062] Embodiment 3: the preparation of phenylpropionaldehyde

[0063] Preparation of 1-(3-methoxyallyl)benzene

[0064] Under nitrogen, bromobenzene (1.6 g, 0.01 mole), magnesium (3.2 g, 0.13 mole), 10 milliliters of tetrahydrofuran and 50 mg of iodine were added to the reaction flask, and the reaction was initiated by heating, and bromobenzene (15.7 g, 0.1 mole) and 60 milliliters of tetrahydrofuran was dripped into the reaction flask and kept boiling slightly. After dropping, the reaction was stirred at 25°C for 3 hours. Cool to room temperature after the reaction, add acrolein dimethyl acetal (10.2 g, 0.1 mol) and cuprous chloride (9.9 g, 0.1 mol), and react under reflux for 12 hours. After the reaction, the pH value was adjusted to 8 with saturated ammonium chloride aqueous solution at 0°C. The tetrahydrofuran was distilled off, 50 ml of ethyl acetate was added, the organic layer was separated, and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The...

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Abstract

The invention relates to a method for preparing aryl propanal derivatives. The aryl propanal derivatives are prepared according to a route shown in the specifications, wherein R1, R2, R3, R4 and R5 independently represent hydrogen, C1 to C4 alkyl, C1 to C4 alkoxy, halogen, trihalogenated methyl or nitro respectively; R6 and R6' independently represent hydrogen, C1 to C4 alkyl, C1 to C4 trihalogenated alkyl, substituted benzyl or alkylacyl respectively, and are connected or not connected; and X represents fluorine, chlorine, bromine or iodine. For the method, raw materials are readily available and have low price, oxidation reaction and reduction reaction are not needed, the route is simple, reaction conditions are mild, the requirement on production equipment is low, the emission of three wastes is low, and industrial production is easy to implement, so the method can be widely applied to the synthesis of medicines, daily chemicals and the like.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular, the invention relates to a preparation method of aryl propionaldehyde derivatives. Background technique [0002] Aryl propionaldehyde derivatives (formula I) are an important class of compounds, which play a very important role in the construction of aryl propyl synthons. For example wherein a kind of specific compound m-trifluoromethylphenylpropionaldehyde (formula a) is exactly the key intermediate of synthetic new drug Sensipar (cinacalcet, cinacalcet, formula b) (see for example US 6211244; Drugs 2002, 27 (9 ), pp. 831-836). The new drug Sensipar is a new drug approved by the FDA for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis and hypercalcemia in patients with parathyroid cancer. The first drug in a new class of compounds called calcimimetics. The drug activates calcium receptors in the parathyroid glands, thereby reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/27C07C47/24C07C47/228C07C47/277
Inventor 陈维翁科杰宋文芳杨建军
Owner 中国中化股份有限公司
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