Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of 3-ethoxy-4-carboxyphenylacetic acid

A technology of ethoxy and carboxybenzene is applied in the field of synthesizing 3-ethoxy-4-carboxyphenylacetic acid, which can solve the problems of large environmental harm and dangerous operation, achieve no toxic and side effects, improve production safety, and reduce costs Effect

Active Publication Date: 2021-08-24
JIANGSU UNIV OF TECH
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the highly toxic substance sodium cyanide is required in the synthetic route of compound II and III, which is dangerous to operate and has great harm to the environment

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of 3-ethoxy-4-carboxyphenylacetic acid
  • A kind of preparation method of 3-ethoxy-4-carboxyphenylacetic acid
  • A kind of preparation method of 3-ethoxy-4-carboxyphenylacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Under the protection of an inert gas, newly prepared magnesium powder (2.43 g, 0.1 mol) was added into a three-necked flask, and 30 mL of newly distilled tetrahydrofuran was added. Separately, 4-bromomethyl-2-ethoxybromobenzene (10.0 g, 0.034 mol) was dissolved in 100 mL of freshly distilled tetrahydrofuran, transferred into a constant pressure dropping funnel, and inserted into a three-necked flask. Under stirring, slowly drop about 30 mL of 4-bromomethyl-2-ethoxybromobenzene tetrahydrofuran solution in a constant-pressure dropping funnel, quickly add 0.05 g of iodine, and slightly heat to about 40°C to initiate the reaction. After the reaction was initiated, the tetrahydrofuran solution of 4-bromomethyl-2-ethoxybromobenzene remaining in the constant pressure dropping funnel was slowly added dropwise, and the temperature was maintained at 60°C. After the dropwise addition, heat to reflux for 18 hours to obtain the double Grignard reagent.

[0031] After cooling the pr...

Embodiment 2

[0033] Under the protection of an inert gas, newly prepared magnesium powder (2.43 g, 0.1 mol) was added into a three-necked flask, and 30 mL of newly distilled ether was added. In addition, 4-chloromethyl-2-ethoxychlorobenzene (2.05g, 0.01mol) was dissolved in 80mL of freshly distilled ether, transferred into a constant pressure dropping funnel, and inserted into a three-necked flask. Under stirring, slowly add about 20 mL of ether solution of 4-chloromethyl-2-ethoxychlorobenzene in a constant pressure dropping funnel, 0.05 g of iodine, and slightly heat to about 40°C to initiate the reaction. After the reaction was initiated, the remaining 4-chloromethyl-2-ethoxychlorobenzene ether solution in the constant pressure dropping funnel was slowly added dropwise, and the temperature was maintained at 60°C. After the dropwise addition, heat to reflux for 18 hours to obtain the double Grignard reagent.

[0034] After cooling the prepared double Grignard reagent to 0°C, slowly pass ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing 3-ethoxy-4-carboxyphenylacetic acid. The bis-Grignard reagent (Ⅴ) is prepared by reacting the dihalogenated compound (Ⅳ) with metallic magnesium firstly. The double Grignard reagent (Ⅴ) reacts with excess carbon dioxide, followed by hydrolysis under acidic conditions to produce 3‑ethoxy‑4‑carboxyphenylacetic acid (I). The preparation method of the invention has easy-to-obtain raw materials, no toxic and side effects, convenient post-treatment and good industrial application value.

Description

technical field [0001] The invention relates to a preparation method of a fine chemical intermediate, in particular to a method for synthesizing 3-ethoxy-4-carboxyphenylacetic acid. Background technique [0002] 3-Ethoxy-4-carboxyphenylacetic acid is an important intermediate in the synthesis of oral hypoglycemic drug repaglinide, and is also listed as repaglinide impurity A by the British Pharmacopoeia. Its structure is shown in the following formula (I): [0003] [0004] The preparation method of 3-ethoxy-4-carboxyphenylacetic acid reported at present all obtains by hydrolysis reaction: [0005] (1) Patent CN 104628518A (2015.05.20) discloses the following synthesis method: [0006] [0007] 3-Ethoxy-4-ethoxycarbonylphenylacetonitrile (II) undergoes simultaneous hydrolysis reaction of ester group and nitrile group under alkaline conditions to obtain 3-ethoxy-4-carboxyphenylacetic acid (I). [0008] (2) Patent CN 101830796B (2015.02.18) and Indian Patent 120 / MUM / 2...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/09C07C65/21
CPCC07C51/09C07F3/02C07C65/21
Inventor 陈超越杨廷海潘长多
Owner JIANGSU UNIV OF TECH