SU843732A3 - Способ получени замещенной инданилуксусной кислоты - Google Patents
Способ получени замещенной инданилуксусной кислоты Download PDFInfo
- Publication number
- SU843732A3 SU843732A3 SU752197008A SU2197008A SU843732A3 SU 843732 A3 SU843732 A3 SU 843732A3 SU 752197008 A SU752197008 A SU 752197008A SU 2197008 A SU2197008 A SU 2197008A SU 843732 A3 SU843732 A3 SU 843732A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetic acid
- lower alkyl
- acid
- water
- hydrogen
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- RJVZEPWRJJBXLH-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)CCC2=C1 RJVZEPWRJJBXLH-UHFFFAOYSA-N 0.000 claims description 3
- -1 2-methyl- (2-isopropyl) -5-indanyl acetonitrile Chemical compound 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims 2
- FFKMFVYNGKOVCG-UHFFFAOYSA-N 2-(2-methyl-2-propan-2-yl-1,3-dihydroinden-5-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=C2CC(C(C)C)(C)CC2=C1 FFKMFVYNGKOVCG-UHFFFAOYSA-N 0.000 claims 1
- HLLKGWROMTWPRD-UHFFFAOYSA-N CCC(C1=CC2=C(CC(C2)C)C=C1)C(=O)O Chemical compound CCC(C1=CC2=C(CC(C2)C)C=C1)C(=O)O HLLKGWROMTWPRD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 4
- MMTOBOVIEKOZHS-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1h-inden-5-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=C2CC(CC)CC2=C1 MMTOBOVIEKOZHS-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- AVLCYTRBQULWGZ-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yl)acetic acid Chemical class OC(=O)CC1=CC=C2CCCC2=C1 AVLCYTRBQULWGZ-UHFFFAOYSA-N 0.000 description 2
- CRVLWWKYIRLIAX-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1h-inden-5-yl)acetonitrile Chemical compound C1=C(CC#N)C=C2CC(CC)CC2=C1 CRVLWWKYIRLIAX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MRASYQFTHLLRCS-UHFFFAOYSA-N 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=C2CC(C(C)C)CC2=C1 MRASYQFTHLLRCS-UHFFFAOYSA-N 0.000 description 1
- LJWXBSNLVNLGIL-UHFFFAOYSA-N 2-(6-chloro-2-ethyl-2-methyl-1,3-dihydroinden-5-yl)acetic acid Chemical compound ClC1=C(CC(O)=O)C=C2CC(CC)(C)CC2=C1 LJWXBSNLVNLGIL-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1525173A CH592598A5 (en, 2012) | 1973-10-30 | 1973-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU843732A3 true SU843732A3 (ru) | 1981-06-30 |
Family
ID=4407595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752197008A SU843732A3 (ru) | 1973-10-30 | 1975-12-10 | Способ получени замещенной инданилуксусной кислоты |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4166131A (en, 2012) |
| JP (3) | JPS5756460B2 (en, 2012) |
| BE (1) | BE821557A (en, 2012) |
| CA (1) | CA1061362A (en, 2012) |
| CH (1) | CH592598A5 (en, 2012) |
| CS (2) | CS183796B2 (en, 2012) |
| DD (1) | DD114058A5 (en, 2012) |
| DE (1) | DE2449928A1 (en, 2012) |
| DK (1) | DK550774A (en, 2012) |
| ES (5) | ES431432A1 (en, 2012) |
| FI (1) | FI59984C (en, 2012) |
| FR (1) | FR2248831B1 (en, 2012) |
| GB (1) | GB1484088A (en, 2012) |
| HU (1) | HU168104B (en, 2012) |
| IE (1) | IE40194B1 (en, 2012) |
| IL (1) | IL45945A (en, 2012) |
| NL (1) | NL7413981A (en, 2012) |
| NO (1) | NO143499C (en, 2012) |
| PH (1) | PH12417A (en, 2012) |
| PL (2) | PL92094B1 (en, 2012) |
| SE (1) | SE418176B (en, 2012) |
| SU (1) | SU843732A3 (en, 2012) |
| ZA (1) | ZA746984B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50111057A (en, 2012) * | 1974-02-14 | 1975-09-01 | ||
| DK470875A (da) * | 1974-10-29 | 1976-04-30 | Sandoz Ag | Fremgangsmade til fremstilling af benzenderivater |
| FR2379511A1 (fr) * | 1977-02-02 | 1978-09-01 | Hexachimie | Sel de lysine de l'acide a-methyl (isopropyl-2 indanyl-5) acetique |
| LU77254A1 (en, 2012) * | 1977-05-04 | 1979-01-18 | ||
| US5179229A (en) * | 1992-04-24 | 1993-01-12 | Hoechst Celanese Corporation | Preparation of 2,2-diorgano-3-arylpropionic acids and esters thereof |
| JP2003083822A (ja) * | 2001-09-10 | 2003-03-19 | Nichiyo Engineering Kk | 締め付けトルク測定方法および装置 |
| US7888381B2 (en) * | 2005-06-14 | 2011-02-15 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity, and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4058622A (en) * | 1972-07-11 | 1977-11-15 | Sumitomo Chemical Company, Limited | Substituted phenyl acetate, insecticidal composition and method of use |
-
1973
- 1973-10-30 CH CH1525173A patent/CH592598A5/xx not_active IP Right Cessation
-
1974
- 1974-10-21 FI FI3073/74A patent/FI59984C/fi active
- 1974-10-21 DE DE19742449928 patent/DE2449928A1/de not_active Withdrawn
- 1974-10-21 NO NO743788A patent/NO143499C/no unknown
- 1974-10-21 DK DK550774A patent/DK550774A/da unknown
- 1974-10-23 SE SE7413366A patent/SE418176B/xx unknown
- 1974-10-24 US US05/517,531 patent/US4166131A/en not_active Expired - Lifetime
- 1974-10-24 GB GB46116/74A patent/GB1484088A/en not_active Expired
- 1974-10-25 NL NL7413981A patent/NL7413981A/xx not_active Application Discontinuation
- 1974-10-25 DD DD181934A patent/DD114058A5/xx unknown
- 1974-10-28 PL PL1974185104A patent/PL92094B1/pl unknown
- 1974-10-28 CA CA212,355A patent/CA1061362A/en not_active Expired
- 1974-10-28 ES ES431432A patent/ES431432A1/es not_active Expired
- 1974-10-28 BE BE149946A patent/BE821557A/xx unknown
- 1974-10-28 IL IL45945A patent/IL45945A/en unknown
- 1974-10-28 PH PH16458A patent/PH12417A/en unknown
- 1974-10-28 IE IE2217/74A patent/IE40194B1/xx unknown
- 1974-10-28 PL PL1974185105A patent/PL92438B1/pl unknown
- 1974-10-29 JP JP49124022A patent/JPS5756460B2/ja not_active Expired
- 1974-10-29 CS CS7500007942A patent/CS183796B2/cs unknown
- 1974-10-29 HU HUSE1668A patent/HU168104B/hu unknown
- 1974-10-29 CS CS7400007369A patent/CS183767B2/cs unknown
- 1974-10-29 FR FR7436068A patent/FR2248831B1/fr not_active Expired
- 1974-10-30 ZA ZA00746984A patent/ZA746984B/xx unknown
-
1975
- 1975-12-10 SU SU752197008A patent/SU843732A3/ru active
-
1976
- 1976-08-02 ES ES450381A patent/ES450381A1/es not_active Expired
- 1976-08-02 ES ES450379A patent/ES450379A1/es not_active Expired
- 1976-08-02 ES ES450382A patent/ES450382A1/es not_active Expired
- 1976-08-02 ES ES450380A patent/ES450380A1/es not_active Expired
-
1981
- 1981-05-08 JP JP6846881A patent/JPS56164138A/ja active Granted
- 1981-05-08 JP JP6846781A patent/JPS56164137A/ja active Granted
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