IES20180106A2 - Drugs intermediates 2-formylcarbonylbenzoic acid synthesis method - Google Patents
Drugs intermediates 2-formylcarbonylbenzoic acid synthesis method Download PDFInfo
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- IES20180106A2 IES20180106A2 IES20180106A IES20180106A IES20180106A2 IE S20180106 A2 IES20180106 A2 IE S20180106A2 IE S20180106 A IES20180106 A IE S20180106A IE S20180106 A IES20180106 A IE S20180106A IE S20180106 A2 IES20180106 A2 IE S20180106A2
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- Prior art keywords
- solution
- formylcarbonylbenzoic
- mass fraction
- acid
- washed
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- 239000000543 intermediate Substances 0.000 title claims abstract description 10
- BVNXSQRWQGKXQJ-UHFFFAOYSA-N 2-oxaldehydoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C=O BVNXSQRWQGKXQJ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 229940079593 drug Drugs 0.000 title claims abstract description 8
- 238000001308 synthesis method Methods 0.000 title claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims abstract description 16
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 12
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims abstract description 12
- WWGUMAYGTYQSGA-UHFFFAOYSA-N 2,3-dimethylnaphthalene Chemical compound C1=CC=C2C=C(C)C(C)=CC2=C1 WWGUMAYGTYQSGA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 7
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 6
- SWDGQFQKNKEWHK-UHFFFAOYSA-N B(F)(F)F.[Ag] Chemical compound B(F)(F)F.[Ag] SWDGQFQKNKEWHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- -1 bonyl benzoic acid Chemical compound 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Drugs intermediates 2-formylcarbonylbenzoic acid synthesis method, comprises the following steps: the reaction vessel was added 3 mole 2,3-dimethylnaphthalene, 1.5 L ethanol solution, and 4-5 mol 3-carboxymethyl, controlling the stirring speed at 110-130 rpm, maintaining the temperature to 40-46°C, keeping for 90-110 min, continuing to add 20g selenium dioxide powder, silver boron fluoride powder 30-50g, raising the solution temperature to 50-58°C, keeping for 130-150 min, filter, washed with potassium bromide solution, washed with isobutyric acid solution, and with methyl chloroacetate solution, dehydrated with the dehydrating agent to obtain 2-formylcarbonylbenzoic acid.
Description
FEELB (JFTHE INVENTION The present invention relates to drugs intermediates 2—formylcarbonylbenzoic acid syntliesis method.
GENERAL BACKGROUND 2-foi‘inyicai‘bonyl benzoic acid is mainly used for chemical reagents, fine chemicals, pharmaceutical intermediates, materials intermediates, however, most of the existing synthetic methods are using naphthalene as reactants, it is complicated and the tiiial yield is not very high. Therefore, it is necessary to propose a new synthetic method for t‘urther improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.
SUMMARY The purpose of the. present invention is to provide drugs intermediates 2~'Formylcai'bonylbenzoic acid synthesis method, comprises the following steps: (i) the reaction vessel was added 3 mole 2,3~dimethylnaphthalene, l.5 L ethanol solution, and 4-5 mol 3—carboxymethyl, controlling the stirring speed at I l0—130 rpm, maintaining the temperature to 40—46°C , keeping for 90-110 min, continuing to add 20g selenium dioxide powder, silver boron fluoride powder 30—50g, raising the solution temperature to 50—58”C, keeping for 130-150 min, filter, washed with potassium bromide solution, washed with isobutyric acid solution, and with methyl chloroacetate solution, dehydrated with the dehydrating agent to obtain 2-formylcarbonylbenzoic acid; wherein, the mass fraction of the ethanol solution in step (i) is 20~27%, the mass iiactioii of the potassium bromide described in step (i) is 10-16%, the mass fraction of he isobutyric acid solution of step (i) is 50-55%, the mass fraction of the methyl chlotoacetate solution in step (i) is 70-78%, the dehydrating agent in step (i) is any one of anhydrous magnesium sulfate and activated alumina. in‘ ;;,;;,»;:sr.'.‘.'>:§:§-.
[\J U‘! Throughout the reaction process can be the following reaction formula: ca, , cecooa S603 \\ / 4 z . —._—‘-‘--‘-—‘-W ’ 1‘i.gBF,; / \COOH \/ ‘COOH Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS The following examples with reference to specific embodiments of the present invention are further illustrated: drugs intermediates 2-formylcarbonylbenzoic acid synthesis method.
Embodiment t The reaction vessel was added 3 mol 2,3—dimethylnaphthalene, 1.5 L ethanol solution with a mass fraction of 20%, 4 mol 3-carboxymethyl, controlled stirring speed at l 10 rpm, kept at 40 “C for 90 min , continue to add 20 g selenium dioxide powder, 3 0g silver borofluoride powder, raising the temperature of the solution to 50“C for 130 min, filter, washed with potassium bromide solution with a mass fraction of 10%, washed with isobutyric acid solution with a mass fraction of 50%, washed with methyl chloroacetate solution with a mass fraction of 70%, and dehydrated with anhydrous magnesium sulfate dehydrating agent to obtain 506.34g 2~formylcarbonylbenzoic acid, yield 87%.
Embodiment 2 The reaction vessel was added 3 mol 2,3—dimethylnaphthalene, 1.5 L ethanol solution with a mass fraction of 23%, 4.5 mol 3—ca1'boxymethyl, controlled stirring speed at l2O rpm, kept at 43 °C for l00 min, continue to add 20 g selenium dioxide powder, 40g silver borofl uoride powder, raising the temperature of the solution to 53 for M0 min, filter, washed with potassium bromide solution with a mass fraction of 13%, washed with isobutyric acid solution with a mass fraction of 52%, washed with methyl chloroacetate solution with a mass fraction of 73%, and dehydrated with activated alumina dehydration agent, 2—t"ormylcarbonyl benzoic acid 529.62g, yield of l %, Embodiment 3 The reaction vessel was added 3 mol 2,3—dimethylnaphthalene, 1.5 L ethanol solution with a. mass fraction of 27%, 5 mol 3—carboxymethyl, controlled stirring speed at l3O rpm, kept at 46 °C for I 10 min , continue to add 20 g selenium dioxide powder, 50g silver borofluoride powder, raising the temperature of the solution to 58"C for 1.50 min, filter, washed with potassium bromide solution with a mass fraction of l6%, washed with isobutyric acid solution with a mass fraction of 55%, washed with methyl chloroacetate solution with a mass fraction of 78%, and dehydrated with anhydrous magnesium sulfate dehydrating agent to obtain 2-formylcarbonyl benzoic l5 acid 541.26g, the yield o[’93%.
Claims (3)
1. Drugs intermediates 2—formylcarbonylbenzoic acid synthesis method, comprises the following steps: (i) the reaction vessel was added 3 mole 2,3-dimethylnaphthalene, 1.5 L ethanol solution, and 4-5 moi 3—carboxymethyl, controlling the stirring speed at 1 10~l30 rpm, maintaining the temperature to 40-46"C, keeping for 90-110 min, continuing to add 20g selenium dioxide powder, silver boron fluoride powder 30—50g, raising the solution temperature to 50~58°C, keeping for 130-150 min, filter, washed with potassium bromide solution, washed with isobutyric acid solution, and with methyl chloroacetate solution, dehydrated with the dehydrating agent to obtain 2—t"ormylcarbonylbenzoic acid; wherein, the mass fraction of the ethanol solution in step (i) is 20-27%, the mass fraction of the potassium bromide described in step (i) is lO—16%, the mass fraction of the isobutyric acid solution of step (i) is 50-55%,
2. Drugs intermediates 2—formylcarbonylbenzoic acid synthesis method according to claim 1 wherein the mass fraction of the methyl chloroacetate solution in step (i) is 70—78%.
3. Drugs intermediates 2—formylcarbonylbenzoic acid synthesis method according to claim 1 wherein the dehydrating agent in step (i) is any one of anhydrous magnesium sulfate and activated alumina.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180106A IES87020B2 (en) | 2018-04-03 | 2018-04-03 | Drugs intermediates 2-formylcarbonylbenzoic acid synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180106A IES87020B2 (en) | 2018-04-03 | 2018-04-03 | Drugs intermediates 2-formylcarbonylbenzoic acid synthesis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IES20180106A2 true IES20180106A2 (en) | 2019-06-12 |
| IES87020B2 IES87020B2 (en) | 2019-06-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IES20180106A IES87020B2 (en) | 2018-04-03 | 2018-04-03 | Drugs intermediates 2-formylcarbonylbenzoic acid synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IES87020B2 (en) |
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2018
- 2018-04-03 IE IES20180106A patent/IES87020B2/en unknown
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| Publication number | Publication date |
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| IES87020B2 (en) | 2019-06-12 |
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