Method for preparing 6-bromotriphenylphosphonio-n-caproic acid

A technology of triphenylphosphine bromide and n-hexanoic acid, which is applied in the fields of chemical instruments and methods, organic chemistry, and compounds of Group 5/15 elements of the periodic table, can solve the problems of pollution and high cost, and achieve cost reduction, Effect of increasing yield and reducing production cost

Active Publication Date: 2017-05-10
黄石市利福达医药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method has high cost and serious

Method used

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  • Method for preparing 6-bromotriphenylphosphonio-n-caproic acid
  • Method for preparing 6-bromotriphenylphosphonio-n-caproic acid

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Embodiment 1

[0049] The present embodiment provides a kind of preparation method of 6-bromotriphenylphosphoryl n-hexanoic acid, the method comprises the following steps:

[0050] 1. Hydrolysis reaction: put 220g of caprolactam and 140g of sodium hydroxide into a 500ml bottle, heat up and reflux for 5 hours, after the reaction is complete, add 230g of water to dilute to obtain a hydrolyzate.

[0051] Add 353g of hydrolyzate to the 1000ml bottle, add dropwise 230g of 30% industrial hydrochloric acid to adjust the pH to 4, pour it out for later use.

[0052] 2. Diazotization reaction: Add 150g of water and 100g of sodium nitrite into a 1000ml bottle, stir to dissolve, lower to -5°C, add the hydrolyzate with adjusted pH dropwise at -5°C to 0°C, and finish adding dropwise in 35 minutes. After the dropwise addition, keep it warm at -5°C to 0°C for 5 hours, then add 42g of 30% industrial hydrochloric acid dropwise, heat up and reflux for 13min until the starch potassium iodide test paper does not...

Embodiment 2

[0057] The present embodiment provides a kind of preparation method of 6-bromotriphenylphosphoryl n-hexanoic acid, the method comprises the following steps:

[0058] 1. Hydrolysis reaction: Put 230g caprolactam and 150g sodium hydroxide into a 500ml bottle, heat up and reflux for 7 hours, after the reaction is complete, add 250g water to dilute to obtain a hydrolyzate.

[0059] Add 353g of hydrolyzate to the 1000ml bottle, add dropwise 245g of 30% industrial hydrochloric acid to adjust the pH to 5, pour it out for later use.

[0060] 2. Diazotization reaction: Add 157g of water and 107g of sodium nitrite into a 1000ml bottle, stir to dissolve, lower to -8°C, add the hydrolyzate with adjusted pH dropwise at -8°C to 0°C, and finish adding dropwise in 40 minutes. After the dropwise addition, keep it warm at -8°C to 0°C for 6 hours, then add 50g of 30% industrial hydrochloric acid dropwise, heat up and reflux for 19min until the starch potassium iodide test paper does not turn blue,...

Embodiment 3

[0065] The present embodiment provides a kind of preparation method of 6-bromotriphenylphosphoryl n-hexanoic acid, the method comprises the following steps:

[0066] 1. Hydrolysis reaction: put 223g caprolactam and 135g sodium hydroxide into a 500ml bottle, heat up and reflux for 7 hours, after the reaction is complete, add 240g water to dilute to obtain a hydrolyzate.

[0067] Add 350g of hydrolyzate to the 1000ml bottle, add dropwise 238g of 30% industrial hydrochloric acid to adjust the pH to 4.7, pour it out for later use.

[0068] 2. Diazotization reaction: Add 154g of water and 104g of sodium nitrite into a 1000ml bottle, stir to dissolve, lower to -2°C, add the hydrolyzate with adjusted pH dropwise at -2°C to 0°C, and finish adding dropwise in 40 minutes. After the dropwise addition, keep it warm at -2°C to 0°C for 7 hours, then add 52g of 30% industrial hydrochloric acid dropwise, heat up and reflux for 13 minutes until the starch potassium iodide test paper does not t...

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Abstract

The invention relates to the field of production and preparation of compounds and particularly relates to a method for preparing 6-bromotriphenylphosphonio-n-caproic acid. The method comprises the following steps: (1) subjecting caprolactam to a hydrolysis reaction, so as to prepare 6-aminocaproic acid; (2) subjecting 6-aminocaproic acid to a diazotization reaction, so as to prepare 6-hydroxycaproic acid; (3) subjecting 6-hydroxycaproic acid to a bromization reaction, so as to prepare 6-bromocaproic acid; and (4) enabling 6-bromocaproic acid to react with triphenyl phosphine, thereby obtaining 6-bromotriphenylphosphonio-n-caproic acid.

Description

technical field [0001] The invention relates to the field of production and preparation of compounds, in particular to a preparation method of 6-bromotriphenylphosphonyl n-hexanoic acid. Background technique [0002] 6-triphenylphosphonyl-n-hexanoic acid bromide is an important intermediate of capsaicin analogue 8-methyl-cis-6-nonenoyl(3,4-dimethoxy)benzylamine, which has analgesic properties , anti-inflammatory, treatment of herpes zoster neuropathy and diabetic neuralgia and other medicinal effects. [0003] The preparation of 6-bromotriphenylphosphine-n-hexanoic acid by traditional process is to prepare 6-hydroxyhexanoic acid from cyclohexene, which is brominated to obtain 6-bromohexanoic acid, and then reacted with triphenylphosphine to obtain 6-bromotriphenyl Phospho-n-hexanoic acid. However, because the yield of this method is only about 10%, the cost is high and the pollution is serious. [0004] In view of this, the present invention is proposed. Contents of the...

Claims

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Application Information

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IPC IPC(8): C07F9/54
CPCC07F9/5442
Inventor 成家钢
Owner 黄石市利福达医药化工有限公司
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