HU184766B - Process for preparing 5-chloro-2-oxo-bicyclo/2,2,1/heptane-7-carboxylic acid alkyl esters - Google Patents
Process for preparing 5-chloro-2-oxo-bicyclo/2,2,1/heptane-7-carboxylic acid alkyl esters Download PDFInfo
- Publication number
- HU184766B HU184766B HU4980A HU4980A HU184766B HU 184766 B HU184766 B HU 184766B HU 4980 A HU4980 A HU 4980A HU 4980 A HU4980 A HU 4980A HU 184766 B HU184766 B HU 184766B
- Authority
- HU
- Hungary
- Prior art keywords
- heptane
- acid
- carboxylic acid
- alcohol
- chloro
- Prior art date
Links
- 125000005907 alkyl ester group Chemical group 0.000 title claims abstract description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000019253 formic acid Nutrition 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 5
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 5
- 150000003180 prostaglandins Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GITMDXBNYPOUCJ-UHFFFAOYSA-N 5-chloro-2-oxobicyclo[2.2.1]heptane-7-carboxylic acid Chemical compound C1C(=O)C2CC(Cl)C1C2C(=O)O GITMDXBNYPOUCJ-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- LIFWFENYWIVVSJ-UHFFFAOYSA-N methyl 5-chloro-2-oxobicyclo[2.2.1]heptane-7-carboxylate Chemical compound C1C(=O)C2CC(Cl)C1C2C(=O)OC LIFWFENYWIVVSJ-UHFFFAOYSA-N 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- POKRQUNDSGAZIA-OALUTQOASA-N 7-[(1r,2s)-2-octylcyclopentyl]hepta-2,4-dienoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCC=CC=CC(O)=O POKRQUNDSGAZIA-OALUTQOASA-N 0.000 description 1
- LCFHHOPZWRFYJY-UHFFFAOYSA-N CCOC(=O)C1C2CC(C1CC2=O)Cl Chemical compound CCOC(=O)C1C2CC(C1CC2=O)Cl LCFHHOPZWRFYJY-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- LKLAOWLOTDVVGF-UHFFFAOYSA-N chromium(6+) oxygen(2-) sulfuric acid Chemical compound [O-2].[O-2].[O-2].[Cr+6].OS(O)(=O)=O LKLAOWLOTDVVGF-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 methyl 5-bromo-2-oxobicyclo [2.2.1] heptane-7-carboxylic acid Chemical compound 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- IDHBLVYDNJDWNO-UHFFFAOYSA-N propyl octanoate Chemical compound CCCCCCCC(=O)OCCC IDHBLVYDNJDWNO-UHFFFAOYSA-N 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS245179A CS202478B1 (en) | 1979-04-10 | 1979-04-10 | Alkylesters of 5-chlor-2-keto-bicyclo/2,2,1/heptane-7-carboxylic acid and method for producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184766B true HU184766B (en) | 1984-10-29 |
Family
ID=5361695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU4980A HU184766B (en) | 1979-04-10 | 1980-01-11 | Process for preparing 5-chloro-2-oxo-bicyclo/2,2,1/heptane-7-carboxylic acid alkyl esters |
Country Status (5)
| Country | Link |
|---|---|
| BG (1) | BG37445A1 (cs) |
| CS (1) | CS202478B1 (cs) |
| DD (1) | DD157508A3 (cs) |
| HU (1) | HU184766B (cs) |
| SU (1) | SU962281A1 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107573228A (zh) * | 2016-07-04 | 2018-01-12 | 沈阳欧利康化学科技有限公司 | 一种光学纯2‑氧代三环[2.2.1.0]‑庚烷‑7‑羧酸的制备方法 |
-
1979
- 1979-04-10 CS CS245179A patent/CS202478B1/cs unknown
- 1979-06-06 BG BG4384779A patent/BG37445A1/xx unknown
- 1979-06-06 SU SU797770630A patent/SU962281A1/ru active
- 1979-06-12 DD DD21359579A patent/DD157508A3/de not_active IP Right Cessation
-
1980
- 1980-01-11 HU HU4980A patent/HU184766B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS202478B1 (en) | 1981-01-30 |
| SU962281A1 (ru) | 1982-09-30 |
| DD157508A3 (de) | 1982-11-17 |
| BG37445A1 (en) | 1985-06-14 |
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