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Synthetic method for allyl alcohol-like compound

A synthesis method and compound technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of harsh reaction conditions, high cost, complicated operation, etc., and achieve safe and reliable production, low production cost, The effect of high reaction yield

Active Publication Date: 2009-08-26
LIAONING ASYMCHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this law, ephedrine compounds are controlled products controlled by the state, and the amount of ephedrine compounds is too large, the raw materials are not easy to purchase, and are not suitable for industrial production. Organic Letters, 2007, Vol.9, No.18, 3523-3525
[0006] 3. Organolithium reagent method: Organolithium reagents are expensive, the reaction conditions are harsh, the product is difficult to separate from impurities and solvents, the post-processing of the product is cumbersome, and the three wastes produced are many, which do not meet the requirements of modern chemical industry. Jpn.KokaiTokkyo Koho, 07082195, 28 Mar 1995, Heisei
[0007] 4. Silicone reagent method: In the presence of dihydrate fluorinated ketones and phosphine ligands, vinyltrimethoxysilane reacts with aldehyde vinylation to generate allyl alcohol compounds. In this method, the phosphine ligands are expensive and the operation is complicated. Little practical value
[0008] 5. Acetylene gas method: This method requires the use of acetylene gas, which is not suitable for industrial production. European Journal of Medicinal Chemistry, 28(6), 473-9; 1993
[0009] The above method is not suitable for large-scale production due to problems such as high cost, difficult purchase of raw materials, low yield, harsh reaction conditions, and serious pollution.

Method used

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  • Synthetic method for allyl alcohol-like compound
  • Synthetic method for allyl alcohol-like compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: Preparation of 1-phenylpropyl-2-en-1-ol

[0033] Add 159.9kg (1.2eq) of 21.2% zinc chloride solution to the 1000L enamel kettle, start stirring, and control the temperature at 20-23 degrees, slowly add 23% vinylmagnesium bromide Grignard reagent 283.9kg ( 2.4eq), the dropwise addition is completed, and the temperature is lowered to 0-5 degrees; the temperature is controlled at 0-5 degrees, and a mixed solution of 22.0kg benzaldehyde (1eq) and 39.2kg tetrahydrofuran (1g / 2mL) is added dropwise to the system; Insulate at 0 to 5 degrees, track until the reaction is complete; cool down the system, terminate the system with 244.0kg 10% sulfuric acid (1.2eq), separate the liquid, concentrate the organic phase until there is no fraction, and use methyl tert-butyl After ether extraction, combine with the concentrated system and wash with water and 10% brine until pH = 6.5, then wash once with 25% brine, dry the organic phase over anhydrous sodium sulfate, filter ...

Embodiment 2

[0034] Example 2: Preparation of 1-(pyridin-3-yl)propyl-2-en-1-ol,

[0035]Add 280.0kg (1.1eq) of 15% zinc chloride solution to the 1000L enamel kettle, start stirring, and control the temperature at 22-24 degrees, slowly add 294.1kg (2.0 eq), the dropwise addition is completed, and the temperature is lowered to 3-6 degrees. Control the temperature at 3-6°C, and add a mixture of 30.0kg (1eq) of pyridine-3-carbaldehyde and 80.1kg of 2-methyltetrahydrofuran (1g / 3mL) dropwise into the system. After dropping, keep warm at 3-6 degrees, and track until the reaction is complete. Cool down the system, terminate the system with 201.3kg (1.1eq) of 15% sulfuric acid, separate the liquids, concentrate the organic phase until there is no distillate, extract the aqueous phase with methyl tert-butyl ether, combine with the concentrated system with water and 10% Wash with brine until pH = 6.3, then wash once with 25% brine, dry the organic phase over anhydrous sodium sulfate, filter with ...

Embodiment 3

[0036] Example 3: Preparation of 1-(furan-3-yl)propyl-2-en-1 alcohol,

[0037] Add 138.3kg (1.5eq) of 20% zinc chloride solution to the 1000L enamel kettle, start stirring, and control the temperature at 25 to 30 degrees, slowly add 222.0kg of vinyl magnesium bromide Grignard reagent dropwise to the system ( 2.5eq), the dropwise addition was completed, and the temperature was lowered to 5-10 degrees. Control the temperature at 5-10 degrees, and add dropwise a mixture of 13.0kg 3-furfural (1eq) and 52.0kg tetrahydrofuran (1g / 4.5mL) into the system. After dropping, keep warm at 5-10 degrees, and track until the reaction is complete. Cool down the system, terminate the system with 99.4kg of 20% sulfuric acid (1.5eq), separate the liquids, concentrate the organic phase until there is no distillate, and extract the aqueous phase, combine with the concentrated system and wash with water and 10% brine until pH = 6.2 Finally, it was washed once with 25% brine, and the organic phas...

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Abstract

The invention aims at providing a synthetic method for an allyl alcohol-like compound. In the method, ethylene group magnesium bromide grignard reagent and solution of zinc chloride are first used for preparing divinyl zinc, then aldehyde substances as shown in a corresponding formula 1 (seen in the diagram) are added to the system, wherein, R1 is (C1-C8) alkyl, (C3-C8) naphthene group, (C2-C8) epoxy group alkyl, (C6-C14) aryl, (C7-C20) aralkyl, (C3-C18)-mixed aryl); the ethylene group is used for synthesizing allyl alcohol-like compound, thus enjoying relatively large implementation value and social and economic values, rational technique, safe and reliable production, high reaction yield, low production cost and adaptability to large-scale industrial production.

Description

(1) Technical field: [0001] The invention relates to a method for synthesizing propylene alcohol compounds. (two) background technology: [0002] Due to the double bond and hydroxyl functional groups in the molecular structure of allyl alcohol compounds, they can participate in various reactions such as oxidation, reduction, esterification, etherification and addition, and synthesize a series of downstream products with a wide range of uses. They are widely used in agricultural chemicals, It has a wide range of uses in medicine, spices and organic synthesis. It is an important intermediate for the synthesis of many drugs and natural products. It is widely used in medicinal chemistry and important intermediates. It has important medicinal value and development prospects, and has attracted much attention from researchers. Propylene alcohol compounds containing aromatic rings and aromatic heterocyclic structures are important intermediates for the synthesis of picaline alkaloi...

Claims

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Application Information

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IPC IPC(8): C07C29/40C07C33/30C07C33/48C07C33/03C07D213/30C07D307/42C07D333/16
Inventor 洪浩张席妮卢江平范金林靳志忠
Owner LIAONING ASYMCHEM LAB CO LTD