Synthesis of 3-(α-methoxy)methenylbenzofuran-2(3h)-one

A technology of methenylbenzene and methoxy, which is applied in the field of synthesis of chemical substances, can solve the problems of low atom economy, loss of products, and inability to increase yield, and achieve the effect of stable and reliable process and increased yield

Inactive Publication Date: 2015-09-09
CHONGQING UNISPLENDOUR CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] 1. Because o-hydroxyphenylacetic acid has a high solubility in acidic aqueous solution, more o-hydroxyphenylacetic acid remains in the water phase, and the yield cannot be increased by salting out or extraction, resulting in low atom economy
[0017] 2. A large amount of salt-containing waste acid is produced, which is difficult to deal with
[0019] 4. The organic phase after washing needs to be dried, the product will be lost, and the waste desiccant needs to be treated separately
[0028] 2. After the reaction is over, the excess sulfuric acid and the by-product sodium sulfate need to be washed with alkaline water and water in turn, resulting in a large amount of saline wastewater
[0029] 3. The organic phase after washing needs to be dried, the product will be lost, and the waste desiccant needs to be treated separately

Method used

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  • Synthesis of 3-(α-methoxy)methenylbenzofuran-2(3h)-one
  • Synthesis of 3-(α-methoxy)methenylbenzofuran-2(3h)-one
  • Synthesis of 3-(α-methoxy)methenylbenzofuran-2(3h)-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Weigh 34.1g (0.2mol) of o-chlorophenylacetic acid, 7.04g (0.02mol) of catalyst 8-hydroxyquinoline copper and 253.6g of sodium hydroxide aqueous solution, put them into the autoclave at one time, and react at 170°C for 2h. After cooling to room temperature, the reaction solution was taken out and neutralized to pH 7 with concentrated hydrochloric acid. Filtrate, dry and recover the filter cake, continue to acidify the filtrate with concentrated hydrochloric acid until the pH value is 1, then transfer it to a three-necked round bottom flask with stirring, thermometer, and condenser tube, the oil bath temperature is 80 °C, and distill under reduced pressure at -0.095Mpa until the acid The water was basically evaporated to dryness, and 200 mL of toluene was added to the residue, and the temperature of the oil bath was adjusted to 115°C. Azeotropic distillation was carried out until no more water was evaporated from the system, and 15 mL of acetic acid was added to continue h...

Embodiment 2

[0057] Weigh 34.1g (0.2mol) of o-chlorophenylacetic acid, 7.04g (0.02mol) of catalyst 8-hydroxyquinoline copper and 253.6g of sodium hydroxide aqueous solution, put them into the autoclave at one time, and react at 170°C for 2h. After cooling to room temperature, the reaction solution was taken out and neutralized to pH 7 with concentrated hydrochloric acid. Filter, dry and recover the filter cake, continue to acidify the filtrate with concentrated hydrochloric acid until the pH value is 1, and then transfer it to a three-neck round bottom flask with stirring, thermometer, and condenser. The water was basically evaporated to dryness, and 250mL of toluene was added to the residue, and the temperature of the oil bath was adjusted to 120°C. Azeotropic distillation was carried out until no more water was evaporated from the system, and 20mL of acetic acid was added to continue heating until no more water was formed. The o-hydroxyl group was detected by HPLC. The content of phenyla...

Embodiment 3

[0059] Weigh 68.2g (0.4mol) of o-chlorophenylacetic acid, 14.08g (0.04mol) of catalyst 8-hydroxyquinoline copper and 507.3g of sodium hydroxide aqueous solution, put them into the autoclave at one time, and react at 170°C for 2h. After cooling to room temperature, the reaction solution was taken out and neutralized to pH 7 with concentrated hydrochloric acid. Filtrate, dry and recover the filter cake, continue to acidify the filtrate with concentrated hydrochloric acid until the pH value is 1, then transfer it to a three-neck round bottom flask with stirring, thermometer, and condenser tube, the oil bath temperature is 100 ° C, and distill under reduced pressure at -0.02Mpa until the acid The water was basically evaporated to dryness, and 500mL of toluene was added to the residue, and the temperature of the oil bath was adjusted to 125°C. Azeotropic distillation was carried out until no more water evaporated from the system, and 30mL of acetic acid was added to continue heating...

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Abstract

A 3-(a-methoxyl) methylene benzofuran-2(3H)-ketone synthesis method comprises the synthesis of O-hydroxy phenylacetic acid, the synthesis of lactone and the synthesis of an end product, with focus on lactone synthesis improvement, such that a three-step reaction is conducted in series without separating or purifying the intermediates - the O-hydroxy phenylacetic acid and the lactone.

Description

technical field [0001] The invention relates to a synthesis process of chemical substances, in particular to a method for synthesizing 3-(α-methoxy)methenylbenzofuran-2(3H)-one. Background technique [0002] (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxymethyl acrylate is an important intermediate in the synthesis of azoxystrobin. 3-(α-Methoxy)methenylbenzofuran-2(3H)-one is the synthesis of (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3 - An important intermediate for methyl methoxyacrylate. The synthesis process of (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxymethyl acrylate is such as a one-pot method: [0003] Starting from 3-(α-methoxy)methylenebenzofuran-2-(3H)-one, it was synthesized by a one-pot method with sodium methoxide and 4,6-2 dichloropyrimidine (DCP), This method takes a long time (about 50h). The chemical reaction formula is: [0004] [0005] The synthesis of 3-(α-methoxy)methenylbenzofuran-2(3H)-one is mainly based on o-chlorophenylac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/83C07C69/14C07C67/08
CPCC07D307/83
Inventor 丁永良邹志刚韩丹邓术清杨莹曹超
Owner CHONGQING UNISPLENDOUR CHEM
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