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Novel synthesis process for 4-phenyl-1-butanol

A technology of phenyl and synthetic formula, which is applied in the field of medicine, can solve the problems of strong corrosion of equipment, low cost of raw materials, difficulty in obtaining high-purity 4-chlorobutanol, etc.

Inactive Publication Date: 2013-05-01
ZHANGJIAGANG JIUMU TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The process route is short and the raw material cost is low, but the reaction of tetrahydrofuran ring-opening to 4-chlorobutanol under the action of HCl takes a long time and the yield is low. Since 4-chlorobutanol is easy to ring-close and return to tetrahydrofuran, it is also easy to polymerize. Therefore it is difficult to obtain high-purity 4-chlorobutanol
[0014] In addition, hydrogen chloride gas is highly corrosive to equipment and poses a safety hazard

Method used

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  • Novel synthesis process for 4-phenyl-1-butanol
  • Novel synthesis process for 4-phenyl-1-butanol
  • Novel synthesis process for 4-phenyl-1-butanol

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 1 g of anhydrous zinc chloride and 78.5 g of acetyl chloride to a 250 ml three-necked flask, add 72 g of tetrahydrofuran dropwise under stirring, cool in an ice bath to keep the temperature below 30 degrees, keep warm for 1 hour after dropping, and distill under reduced pressure with a water pump 145 g of ethyl 4-chlorobutanol was obtained with a yield of 96% and a purity of 99.5%.

[0032] Add 30 grams of ethyl 4-chlorobutanol and 78 grams of benzene into a 250-milliliter three-necked flask respectively, cool to 0 degrees under stirring, add 30 grams of anhydrous aluminum trichloride in batches, and control the temperature below 10 degrees. After the addition, the temperature was kept at 10°C for 3 hours, and the reaction of the raw materials was detected by gas phase detection. The reaction solution was slowly poured into crushed ice for hydrolysis, stirred for 30 minutes, and the organic phase was separated. The organic phase was washed with water and saturated ...

Embodiment 2

[0034] Add 1 gram of anhydrous zinc chloride and 78.5 grams of acetyl chloride to a 1000 ml three-necked flask, add 72 grams of tetrahydrofuran dropwise under stirring, cool in an ice bath to keep the temperature below 30 degrees, and keep warm for 1 hour after the drop to complete the reaction. Gas phase detection The content of 4-chlorobutanol acetate is 97%. 390 g of benzene was added to the reaction solution, and the temperature was lowered to 0°C. Add 160 grams of aluminum trichloride in batches, keeping the temperature below 10 degrees. After insulated for 3 hours, the raw materials were detected by gas chromatography and disappeared. The reaction solution was slowly poured into ice water for hydrolysis, stirred for 30 minutes, the organic phase was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After the benzene was removed by distillation, the oil pump decompressed distillation to obtain 144 grams of colorless liquid phe...

Embodiment 3

[0036] Add 1 gram of anhydrous zinc chloride and 141 grams of benzoyl chloride to a 250 ml three-necked bottle, add 72 grams of tetrahydrofuran dropwise at room temperature under stirring, keep it stable below 40 degrees during the dropping process, keep warm for 2 hours after the dropping, and depressurize Distilled to obtain 200 g of 4-chlorobutanol benzoate with a yield of 94% and a purity of 99.35%.

[0037] Add 42.5 grams of 4-chlorobutanol benzoate and 78 grams of benzene into a 250-milliliter three-neck flask respectively, cool to 0 degrees under stirring, add 30 grams of anhydrous aluminum trichloride in batches, and control the temperature below 10 degrees. After the addition, the temperature was kept below 10 degrees for 3 hours, and the reaction of the raw materials was detected by gas phase detection. The reaction solution was slowly poured into crushed ice for hydrolysis, stirred for 30 minutes, and the organic phase was separated. The organic phase was washed wi...

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Abstract

The invention provides a novel synthesis process for 4-phenyl-1-butanol. According to the process, tetrahydrofuran is used as a raw material and rapidly and moderately reacts with acyl chloride under catalysis of zinc chloride so as to obtain high-yield high-purity 4-chlrobutanol ester; without separation, 4-chlrobutanol ester and benzene undergo Friedel-Crafts alkylation under catalysis of aluminum trichloride to obtain 4-phenyl-butanol ester; and 4-phenyl-butanol ester undergoes hydrolysis under an alkaline condition so as to produce 4-phenyl-1-butanol. The process has the advantages of easiness, greenness, environment-friendliness, safety and low cost.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine and relates to a preparation method of 4-phenyl-1-butanol. 2. Technical Background [0002] 4-Phenyl-1-butanol is widely used in medicine, pesticides, dyes, spices and other industries, and is an important intermediate for the synthesis of many compounds. This product is a key intermediate for the treatment of asthma drugs - Prenzast, long-acting β2-receptor agonist salmeterol and other drugs, and can also be used to synthesize caffeic acid phenylbutanol ester with anti-tumor activity. In order to find a synthetic method with high yield and low cost, extensive research has been carried out, and many synthetic methods have been proposed, but there is still no relatively perfect synthetic route. In the early 1950s, Searles reported a synthetic route to prepare phenyl-n-butanol by Grignard reaction using benzyl chloride and 1,3-propylene oxide as raw materials. Subsequently, Detar and Weis and ...

Claims

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Application Information

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IPC IPC(8): C07C33/20C07C27/02
Inventor 敬炳文钱海书赵正达刘春雨周婷
Owner ZHANGJIAGANG JIUMU TECH
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