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

Preparation method of 2,3-bihydrogen-1-indenone and its derivative

A derivative and indanone technology, applied in the field of organic compound preparation chemistry, can solve the problems of increased production cost, troublesome product separation, complicated operation, etc., and achieve the effects of less pollution, low cost and simple process

Inactive Publication Date: 2009-06-10
武汉中新同和科技有限责任公司
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3-aryl acid chloride is prepared from 3-aryl propionic acid, which will inevitably increase the production cost
[1, Nguy, Nim Ming; Chiu, I.C.; Kohn, Harold. Journal of Organic Chemistry (1987), 52(9), 1649-55.2, Horwell, David C.; Howson, William; Nolan, William P.; Ratcliffe , Giles S.; Rees, David C.; Willems, Henriette M.G.Tetrahedron (1995), 51 (1), 203-16.] But use these to make catalyst, complicated operation, will add a large amount of water after reaction finishes, and use a large amount of solvent extraction
This will inevitably produce a large amount of acid wastewater
And product separation is very troublesome
In addition, their corrosion to equipment is also serious.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 3.08g (20mmol) of 3-phenylpropionic acid, 3g (1mmol) of silicotungstic acid and 60ml of toluene into a flask. Install the water separator, reflux the condenser, heat and reflux for dehydration. After the reaction, the insoluble solid was removed by filtration and washed with chloroform, and the organic phases were combined and washed with 60 ml of 2N sodium hydroxide. The aqueous phase was acidified to pH=2 with concentrated hydrochloric acid, extracted with 60 ml of ethyl acetate, evaporated to remove the ethyl acetate, and recrystallized with ethanol to obtain 0.43 g of 3-phenylpropionic acid. The organic phase was evaporated to remove the solvent. A light yellow solid was obtained, which was recrystallized from ethanol to obtain 2.0 g of 2,3-dihydro-1-indanone with a melting point of 38-40°C, a conversion rate of 86%, and a yield of 76%.

Embodiment 2

[0017] 3.68g (20mmol) of 3-p-methoxyphenylpropionic acid, 14g (5mmol) of aluminophosphoric acid and 60ml of benzene were added to a flask. Install the water separator, reflux the condenser, heat and reflux for dehydration. After the reaction, the insoluble solid was removed by filtration and washed with chloroform, and the organic phases were combined and washed with 60 ml of 2N sodium hydroxide. The aqueous phase was acidified with concentrated hydrochloric acid to pH = 2, then extracted with 60 ml of ethyl acetate, evaporated to remove the ethyl acetate, and recrystallized with ethanol to obtain 2.39 g of 3-p-methoxyphenylpropionic acid. The organic phase was evaporated to remove the solvent. A light yellow solid was obtained, which was recrystallized from ethanol to obtain 0.91 g of 6-methoxy-2,3-dihydro-1-indanone, with a melting point of 106-108°C, a conversion rate of 35%, and a yield of 28%.

Embodiment 3

[0019] Add 3.68g (20mmol) of 3-m-methoxyphenylpropionic acid, 14.4g (5mmol) of silicotungstic acid and 60ml of toluene into a flask. Install the water separator, reflux the condenser, heat and reflux for dehydration. After the reaction, the insoluble solid was removed by filtration and washed with chloroform, and the organic phases were combined and washed with 60 ml of 2N sodium hydroxide. The aqueous phase was acidified with concentrated hydrochloric acid to pH = 2, then extracted with 60 ml of ethyl acetate, evaporated to remove the ethyl acetate, and recrystallized from ethanol to obtain 1.0 g of 3-methoxyphenylpropionic acid. The organic phase was evaporated to remove the solvent. A light yellow solid was obtained, which was recrystallized from ethanol to obtain 2.2 g of 6-methoxy-2,3-dihydro-1-indanone, with a melting point of 108-110°C, a conversion rate of 73%, and a yield of 67%.

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 present invention relates to a method for preparing indanone and its derivative by using 3-aryl propionic acid through heteropolyacid catalytic cyclodehydration process. It is characterized by that said method includes the following steps: in the presence of catalyst heteropolyacid making 3-aryl propionic acid and aromatic hydrocarbon undergo the process of refluxing dehydration, filtering to remove heteropolyacid, washing with sodium hydroxide solution and purifying organic phase so as to obtain indanone and its derivative. Its conversion rate is 35-86% and its total yield rate is 28-76%.

Description

technical field [0001] The invention relates to a method for preparing 2,3-dihydro-1-indanone and its derivatives from 3-aryl propionic acid through heteropolyacid-catalyzed cyclodehydration, and belongs to the field of organic compound preparation chemistry. Background technique [0002] 2,3-Dihydro-1-indanone and its derivatives are very important organic intermediates. They are widely used in pharmaceutical chemical industry, catalytic ligands, liquid crystal materials and other fields. [0003] There are many preparation methods for 2,3-dihydro-1-indanone and its derivatives. Among them, the simplest and most convenient method is cyclization via Friedel-Crafts reaction. The Friedel-Crafts reaction cyclization method is mainly divided into two categories, one: cyclization by 3-aryl acid chloride. [Chinese patent CN1471504, Chinese patent CN1762957]. Two: Cyclization by 3-arylpropionic acid. 3-aryl acid chlorides are prepared from 3-aryl propionic acid again, which in...

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): C07C49/67C07C45/46
Inventor 兰鲲王先宝周松耿建国
Owner 武汉中新同和科技有限责任公司