IL41380A - Preparation of 2-alkoxy-5-alkylsulphonyl-benzoic acids - Google Patents
Preparation of 2-alkoxy-5-alkylsulphonyl-benzoic acidsInfo
- Publication number
- IL41380A IL41380A IL41380A IL4138073A IL41380A IL 41380 A IL41380 A IL 41380A IL 41380 A IL41380 A IL 41380A IL 4138073 A IL4138073 A IL 4138073A IL 41380 A IL41380 A IL 41380A
- Authority
- IL
- Israel
- Prior art keywords
- alkoxy
- preparation
- alkylsulphonyl
- methoxy
- uene
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 239000012286 potassium permanganate Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 235000019628 coolness Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BXWLVQXAFBWKSR-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoic acid Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(O)=O BXWLVQXAFBWKSR-UHFFFAOYSA-N 0.000 description 1
- VLEKYZFNWIUBGE-UHFFFAOYSA-N 4-bromo-1-ethoxy-2-methylbenzene Chemical compound CCOC1=CC=C(Br)C=C1C VLEKYZFNWIUBGE-UHFFFAOYSA-N 0.000 description 1
- UDLRGQOHGYWLCS-UHFFFAOYSA-N 4-bromo-1-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Br)C=C1C UDLRGQOHGYWLCS-UHFFFAOYSA-N 0.000 description 1
- SQCYJSHYEZPTKS-UHFFFAOYSA-N 4-ethylsulfonyl-1-methoxy-2-methylbenzene Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C)=C1 SQCYJSHYEZPTKS-UHFFFAOYSA-N 0.000 description 1
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XKLZGOVSPMNRJQ-UHFFFAOYSA-N C(C)SCC.[Cu] Chemical compound C(C)SCC.[Cu] XKLZGOVSPMNRJQ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VPIJTROCWADCRU-UHFFFAOYSA-N copper;methylsulfanylmethane Chemical compound [Cu].CSC VPIJTROCWADCRU-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1080372A CH565758A5 (es) | 1972-07-19 | 1972-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41380A0 IL41380A0 (en) | 1973-03-30 |
| IL41380A true IL41380A (en) | 1977-03-31 |
Family
ID=4367024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41380A IL41380A (en) | 1972-07-19 | 1973-01-24 | Preparation of 2-alkoxy-5-alkylsulphonyl-benzoic acids |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3878240A (es) |
| JP (2) | JPS4935356A (es) |
| AR (1) | AR192695A1 (es) |
| AT (1) | AT321891B (es) |
| AU (1) | AU469248B2 (es) |
| BE (1) | BE793689A (es) |
| BG (1) | BG20097A3 (es) |
| CA (1) | CA993885A (es) |
| CH (1) | CH565758A5 (es) |
| CS (1) | CS181716B2 (es) |
| DD (1) | DD101665A5 (es) |
| DE (1) | DE2259239A1 (es) |
| EG (1) | EG11125A (es) |
| ES (1) | ES409349A1 (es) |
| FR (1) | FR2163301A5 (es) |
| GB (1) | GB1364404A (es) |
| HU (1) | HU174964B (es) |
| IE (1) | IE37364B1 (es) |
| IL (1) | IL41380A (es) |
| IT (1) | IT1048404B (es) |
| LU (1) | LU66805A1 (es) |
| MC (1) | MC960A1 (es) |
| NL (1) | NL7216405A (es) |
| NO (1) | NO138947C (es) |
| OA (1) | OA04328A (es) |
| PL (1) | PL85122B1 (es) |
| RO (1) | RO62849A (es) |
| SE (1) | SE402454B (es) |
| YU (1) | YU36496B (es) |
| ZA (1) | ZA73142B (es) |
| ZM (1) | ZM1073A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609712A (en) * | 1984-06-18 | 1986-09-02 | General Electric Company | Method for preparing monomeric and polymeric bis(dicarboxyphenyl) sulfone compounds |
| US4625013A (en) * | 1984-12-20 | 1986-11-25 | General Electric Company | Aromatic sulfoxy compositions and method for their preparation |
| US4898973A (en) * | 1985-03-07 | 1990-02-06 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| GB9310699D0 (en) * | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Chemical process |
| KR100809489B1 (ko) * | 2001-10-10 | 2008-03-03 | 씨제이제일제당 (주) | 사이클로옥시게나제-2의 저해제로서 선택성이 뛰어난4'-메탄설포닐-비페닐 유도체 |
| AU2003286183A1 (en) * | 2002-12-23 | 2004-07-22 | Dsm Fine Chemicals Austria Nfg Gmbh And Co Kg | Method for producing optionally substituted benzoic acids |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| NL7008629A (es) * | 1969-06-25 | 1970-12-29 | ||
| NL7008630A (es) * | 1969-06-25 | 1970-12-29 |
-
0
- BE BE793689D patent/BE793689A/xx not_active IP Right Cessation
-
1972
- 1972-07-19 CH CH1080372A patent/CH565758A5/xx not_active IP Right Cessation
- 1972-11-22 SE SE7215174A patent/SE402454B/xx unknown
- 1972-11-22 NO NO4265/72A patent/NO138947C/no unknown
- 1972-11-27 PL PL1972159123A patent/PL85122B1/pl unknown
- 1972-11-30 BG BG22006A patent/BG20097A3/xx unknown
- 1972-11-30 HU HU72RE522A patent/HU174964B/hu unknown
- 1972-12-01 NL NL7216405A patent/NL7216405A/xx unknown
- 1972-12-04 DE DE2259239A patent/DE2259239A1/de active Pending
- 1972-12-05 YU YU03014/72A patent/YU36496B/xx unknown
- 1972-12-06 CS CS7200008354A patent/CS181716B2/cs unknown
- 1972-12-06 ES ES409349A patent/ES409349A1/es not_active Expired
- 1972-12-08 RO RO7200073084A patent/RO62849A/ro unknown
- 1972-12-12 AR AR245595A patent/AR192695A1/es active
- 1972-12-13 AT AT1061872A patent/AT321891B/de not_active IP Right Cessation
- 1972-12-18 US US315842A patent/US3878240A/en not_active Expired - Lifetime
- 1972-12-29 FR FR7246873A patent/FR2163301A5/fr not_active Expired
-
1973
- 1973-01-08 ZA ZA730142A patent/ZA73142B/xx unknown
- 1973-01-08 AU AU50863/73A patent/AU469248B2/en not_active Expired
- 1973-01-09 LU LU66805A patent/LU66805A1/xx unknown
- 1973-01-09 CA CA160,847A patent/CA993885A/en not_active Expired
- 1973-01-18 DD DD168316A patent/DD101665A5/xx unknown
- 1973-01-24 IL IL41380A patent/IL41380A/en unknown
- 1973-01-25 ZM ZM10/73A patent/ZM1073A1/xx unknown
- 1973-01-30 MC MC1028A patent/MC960A1/xx unknown
- 1973-02-02 OA OA54822A patent/OA04328A/xx unknown
- 1973-02-06 JP JP48014355A patent/JPS4935356A/ja active Pending
- 1973-02-21 GB GB846773A patent/GB1364404A/en not_active Expired
- 1973-02-28 IT IT7320973A patent/IT1048404B/it active
- 1973-03-02 IE IE340/73A patent/IE37364B1/xx unknown
- 1973-04-03 JP JP48037497A patent/JPS5222B2/ja not_active Expired
- 1973-07-15 EG EG276/73A patent/EG11125A/xx active
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