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New method for synthesizing p-isopropyl benzoic acid

A technology of isopropyl benzoic acid and a new method, which is applied in the field of synthesizing p-isopropyl benzoic acid, can solve problems such as difficult recovery of acetic anhydride, few deep-processed products, and high price of acetic anhydride, and achieve abundant raw materials, low cost, and low price. cheap effect

Inactive Publication Date: 2007-02-21
ZHEJIANG SHUREN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction yield is high, but the price of the solvent acetic anhydride is relatively expensive, the recovery of acetic anhydride is difficult, and the pollution is large; and the reaction is carried out at 90°C for 24 hours, which consumes a lot of energy and takes a long time
[0004] my country is rich in turpentine resources, but there are few deep-processed products. The high-purity β-pinene (β-pinene) isolated from it has not been used in large quantities with high added value. Most of them are exported as low-priced raw materials and processed into high-value fine chemicals. Selling to my country, resulting in foreign exchange loss

Method used

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  • New method for synthesizing p-isopropyl benzoic acid
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Dissolve 4g of sodium hydroxide and 45g of potassium permanganate in 450mL of water, and add 13.6g of β-pinene in batches under vigorous stirring. Use a water bath to maintain the reaction temperature at 25-30°C, react for 3-5 hours, and finish the reaction with potassium permanganate as the end point. The precipitated manganese dioxide was filtered off and washed several times with water. The filtrate was concentrated to 150 mL by evaporation under reduced pressure, and left overnight in the refrigerator. Filtrate under reduced pressure and wash with a small amount of ice water to obtain white norpinate sodium crystals.

[0020] Add the sodium pinoleate obtained above into a mixture of 20 mL of water and 25 mL of dichloromethane, adjust to strong acidity with 6 mol / L hydrochloric acid solution, separate the dichloromethane, wash the aqueous phase three times with 7 mL of dichloromethane, combine the organic phases, Add 5 g of anhydrous sodium sulfate to dry for 1 h, ...

Embodiment 2

[0024] Dissolve 6g of sodium hydroxide and 45g of potassium permanganate in 350mL of water, and add 13.6g of β-pinene in batches under vigorous stirring. Use a water bath to maintain the reaction temperature at 25-30°C, react for 3-5 hours, and finish the reaction with potassium permanganate as the end point. The precipitated manganese dioxide was filtered off and washed several times with water. The filtrate was concentrated to 150 mL by evaporation under reduced pressure, and left overnight in the refrigerator. Filtrate under reduced pressure and wash with a small amount of ice water to obtain 6.5 g of white norpinate sodium crystals.

[0025] Add 10g of norpinate sodium to 200mL 20% sulfuric acid aqueous solution to reflux for 2h, cool and filter to obtain 7g of dihydrocuminic acid.

[0026] Put 80g of dihydrocuminic acid, 3.0g of 7.5% Pd-C catalyst, and 150mL of p-cymene into a 250mL three-necked flask equipped with a thermometer, a stirring magnet, and a condenser tube....

Embodiment 3

[0028] The melting point, hydrogen spectrum and mass spectrum data of the product of embodiment 1,2 are as follows:

[0029] Melting point: 117~119℃

[0030] Hydrogen spectrum: 1 H NMR (CDCl 3 ): δ=1.26(d, 6H, J=6.9Hz); 2.97(m, 1H, J=6.9Hz); 7.30(d, 2H, J=8.2Hz); 8.02(d, 2H, J=8.2Hz ).

[0031] Mass spectrum: MS (m / z): 164 (M + , 42.0), 149(100), 131(22.4), 119(51.8), 105(47.2), 91(18.7), 77(28.2), 65(4.8), 51(7.4), 39(8.0), 27 (5.0).

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Abstract

This invention relates to a method for synthesizing cuminic acid. The method comprises: oxidizing beta-pinene with an oxidant to obtain nopinic acid, dehydrating and ring-opening nopinic acid with sulfuric acid to obtain dihydrocumic acid, and catalytically dehydrogenating to obtain cuminic acid. The method uses recycleable natural product of beta-pinene as the raw material, thus has such advantages as wide raw materials, easy operation, low cost and high utility of beta-pinene.

Description

technical field [0001] The invention relates to a new method for synthesizing p-isopropylbenzoic acid. Background technique [0002] p-Cymenic acid is an important fine chemical, used as a preservative and protective agent in the wood industry, can be used for wastewater treatment and inhibit corrosion of automobile antifreeze; it is also a no-clean flux and certain Raw materials for some polymer thermistors. Especially in recent years, p-isopropylbenzoic acid has been widely used in chemical industries such as medicine, and is an important chemical raw material, such as the new anti-diabetic drug nateglinide, which was launched in Japan in 1999, and the first clinical drug in phase II. Cariporide (HOE-642), a selective NHE-1 inhibitor, was synthesized from p-isopropylbenzoic acid. [0003] Now the synthesis of p-cymenic acid generally takes cumene or p-cymene as raw material. The synthesis of cumene as raw material mainly contains the following 4 routes: (1) chloromethyl...

Claims

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Application Information

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IPC IPC(8): C07C63/04C07C51/16
Inventor 金建忠
Owner ZHEJIANG SHUREN UNIV
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