Method for preparing 4-alkoxy-1-chlorobutane

A technology of alkoxy and chlorobutane, which is applied in the field of preparation of 4-alkoxy-1-chlorobutane, can solve the problems of difficult product refining, difficult catalyst, difficult cleaning, etc. The effect of easy handling and less usage

Inactive Publication Date: 2010-12-29
GAOYOU CITY ORGANIC CHEM FACOTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned organic base catalyst also has shortcoming, mainly is that catalyst is difficult to separate from reaction system after reaction finishes, as dimethyl aniline etc. even use a large amount of water to also be difficult to wash, bring difficulty to the refinement of product

Method used

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  • Method for preparing 4-alkoxy-1-chlorobutane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of 4-methoxy-1-chlorobutane

[0015] Add 104g (1mol) 4-methoxy-butanol, 5 grams of tetramethylammonium chloride and 200ml hexanaphthene in the 500ml four-necked bottle that is furnished with thermometer and dropping funnel; Maintain reaction temperature 65~70 ℃, Stir and slowly add thionyl chloride 131g (1.1mol) dropwise for about 3 hours. After the waste acid tail gas is discharged, the alkali water is absorbed. After the drop is completed, keep stirring and react for 2 hours. Cool down to room temperature, wash the organic phase with 100ml of water, 50ml of saturated sodium bicarbonate, and 50ml of water, recover the solvent cyclohexane under reduced pressure, and distill and collect the fraction of bp114~117℃ to obtain the product 4-methoxy-1-chlorobutane 116.3 grams, gas chromatography content 99.1%, yield 94.1%.

[0016] 1 HNMRδ (ppm): 1.61 (m, 2H, -CH 2 -C-C-Cl), 1.75 (m, 2H, -CH 2 -C-Cl), 3.25(s, 3H, CH 3 -O), 3.35(t, 2H, O-CH ...

Embodiment 2

[0018] Embodiment 2: the preparation of 4-ethoxy-1-chlorobutane

[0019] Add 118g (1mol) of 4-ethoxyl-1-butanol, 8 grams of tetraethylammonium chloride and 200ml of cyclohexane in a 500ml four-necked bottle equipped with a thermometer and a dropping funnel; maintain the reaction temperature at 65-70 ℃, stirred and slowly added thionyl chloride 131g (1.1mol) dropwise, and the drop was completed in about 3 hours. After the waste acid tail gas was discharged, the alkaline water was absorbed, and after the drop was completed, it was incubated and stirred for 2 hours. Cool down to room temperature, wash the organic phase with 100ml of water, 50ml of saturated sodium bicarbonate, and 50ml of water, recover the solvent cyclohexane under reduced pressure, and distill and collect the bp83~86℃ / 100mmHg fraction to obtain the product 4-ethoxy-1-chloro 129.2 grams of butane, gas chromatography content 99.2%, yield 93.9%.

[0020] 1 HNMRδ (ppm): 1.09 (tri, 3H, CH 3 -), 1.63 (m, 2H, -CH ...

Embodiment 3

[0022] Embodiment 3: the preparation of 4-propoxy-1-chlorobutane

[0023] Add 132g (1mol) 4-propoxy-1-butanol, 8 grams of tetrabutylammonium chloride and 250ml toluene in the 500ml four-necked bottle that is furnished with thermometer and dropping funnel; Maintain reaction temperature 65~70 ℃, Stir and slowly add thionyl chloride 131g (1.1mol) dropwise for about 3 hours. After the waste acid tail gas is discharged, the alkali water is absorbed. After the drop is completed, keep stirring and react for 2 hours. Cool down to room temperature, wash the organic phase with 100ml of water, 50ml of saturated sodium bicarbonate, and 50ml of water, recover the solvent toluene under reduced pressure, and distill and collect the bp93~95℃ / 90mmHg fraction to obtain the product 4-propoxy-1-chlorobutane 139.5 grams, gas chromatography content 99.1%, yield 91.9%.

[0024] 1 HNMRδ (ppm): 0.84 (tri, 3H, CH 3 -), 1.53 (m, 2H, 2H, CH 3 -CH 2 * -CH 2 -O-), 1.59 (m, 2H, -CH 2 -C-C-Cl), 1.73 ...

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Abstract

The invention discloses a preparation method for 4-alkoxy-1-chlorobutane used as a synthetic resin raw material and a pharmaceutical intermediate compound. The prior method adopting basic catalyst has shortcomings that: the basic catalyst is difficult to be separated from the reaction system when the reaction is completed, and is difficult to be cleaned even if a large amount of water is used, thereby which brings difficulties to the fine purification for the product. The invention adopts 4-alkoxy-1-chlorobutane as the raw material, which is reacted with thionyl chloride under the existence of quaternary ammonium salt catalyst so as to get the product 4-alkoxy-1-chlorobutane, and then the product is implemented with water scrubbing and stratification for removing the catalyst and destroying the superfluous thionyl chloride, and then the product is washed with lye and water, and the pure product is obtained after distilled in atmospheric pressure and pressure reduction finally. The invention has the advantages of less secondary reaction, convenient post treatment since the product is implemented with water scrubbing and stratification for removing the catalyst and destroying the superfluous thionyl chloride, good catalytic result of the catalyst, less use amount of thionyl chloride, and high content and yield of the product.

Description

technical field [0001] The invention discloses a preparation method of a compound 4-alkoxyl-1-chlorobutane used as a synthetic resin raw material and a pharmaceutical intermediate. Background technique [0002] 4-Alkoxy-1-chlorobutane is a raw material for synthetic resins and an important pharmaceutical intermediate. Its preparation method is usually prepared by chlorination of the corresponding 4-alkoxy-1-butanol. The commonly used chlorination The reagents are phosphorus trichloride and thionyl chloride. [0003] [0004] In comparison, thionyl chloride is widely used because of its cheap and easy-to-obtain raw materials and high chlorination yield. When using thionyl chloride as a raw material for chlorination, usually its amount is slightly more than the raw material alcohol, and the reaction can be carried out in a solvent-free state, or in the presence of an inert solvent such as alkanes, halogenated alkanes, or aromatics and halogena...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/12C07C41/22
Inventor 瞿军陆文辉吴宏祥章学兵顾天猛沈润溥
Owner GAOYOU CITY ORGANIC CHEM FACOTRY
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