CH481091A - Verfahren zur Herstellung von neuen Ketosäuren - Google Patents
Verfahren zur Herstellung von neuen KetosäurenInfo
- Publication number
- CH481091A CH481091A CH584166A CH584166A CH481091A CH 481091 A CH481091 A CH 481091A CH 584166 A CH584166 A CH 584166A CH 584166 A CH584166 A CH 584166A CH 481091 A CH481091 A CH 481091A
- Authority
- CH
- Switzerland
- Prior art keywords
- filtered
- hydrochloric acid
- acid
- solution
- friedel
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000004715 keto acids Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229940014800 succinic anhydride Drugs 0.000 claims description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 4
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 3
- BWCJVGMZEQDOMY-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1-benzofuran Chemical compound C1=CC=C2OC(C)CC2=C1 BWCJVGMZEQDOMY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001907 coumarones Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- DNWQESYPNMYPBK-UHFFFAOYSA-N 2-methoxy-1-benzofuran Chemical class C1=CC=C2OC(OC)=CC2=C1 DNWQESYPNMYPBK-UHFFFAOYSA-N 0.000 claims description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical group CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- QPLLPLLBBSWRTM-UHFFFAOYSA-N 7-methoxy-1-benzofuran Chemical compound COC1=CC=CC2=C1OC=C2 QPLLPLLBBSWRTM-UHFFFAOYSA-N 0.000 description 2
- 241001473317 Eupatorium cannabinum Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940124571 cholagogue Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- LQJRWEBUMYCBBV-UHFFFAOYSA-N 7-methoxy-2,3-dihydro-1-benzofuran Chemical compound COC1=CC=CC2=C1OCC2 LQJRWEBUMYCBBV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000008845 cholagoga Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IXZFDJXHLQQSGQ-UHFFFAOYSA-N ethyl 4-chloro-4-oxobutanoate Chemical compound CCOC(=O)CCC(Cl)=O IXZFDJXHLQQSGQ-UHFFFAOYSA-N 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT954465 | 1965-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH481091A true CH481091A (de) | 1969-11-15 |
Family
ID=11131942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH584166A CH481091A (de) | 1965-04-28 | 1966-04-22 | Verfahren zur Herstellung von neuen Ketosäuren |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT258279B (cs) |
| BE (1) | BE680135A (cs) |
| CH (1) | CH481091A (cs) |
| ES (1) | ES325860A1 (cs) |
| FR (1) | FR5344M (cs) |
| SE (1) | SE326195B (cs) |
-
1966
- 1966-04-20 FR FR58317A patent/FR5344M/fr not_active Expired
- 1966-04-22 CH CH584166A patent/CH481091A/de not_active IP Right Cessation
- 1966-04-22 ES ES0325860A patent/ES325860A1/es not_active Expired
- 1966-04-27 AT AT396566A patent/AT258279B/de active
- 1966-04-27 SE SE05690/66A patent/SE326195B/xx unknown
- 1966-04-27 BE BE680135D patent/BE680135A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES325860A1 (es) | 1967-03-01 |
| BE680135A (cs) | 1966-10-03 |
| FR5344M (cs) | 1967-10-09 |
| SE326195B (cs) | 1970-07-20 |
| AT258279B (de) | 1967-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |