DE2232349A1 - Verfahren zur herstellung von 2-/ omega-alkoxycarbonylalkyl/-2-cyklopenten1-onen - Google Patents
Verfahren zur herstellung von 2-/ omega-alkoxycarbonylalkyl/-2-cyklopenten1-onenInfo
- Publication number
- DE2232349A1 DE2232349A1 DE2232349A DE2232349A DE2232349A1 DE 2232349 A1 DE2232349 A1 DE 2232349A1 DE 2232349 A DE2232349 A DE 2232349A DE 2232349 A DE2232349 A DE 2232349A DE 2232349 A1 DE2232349 A1 DE 2232349A1
- Authority
- DE
- Germany
- Prior art keywords
- alkoxycarbonylalkyl
- mol
- general formula
- bromine derivative
- ones
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 230000031709 bromination Effects 0.000 title description 3
- 238000005893 bromination reaction Methods 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 50
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012442 inert solvent Substances 0.000 claims abstract description 5
- 238000009835 boiling Methods 0.000 claims abstract description 3
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- -1 for example Substances 0.000 claims description 10
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- KZBPPOPPFUDSOP-UHFFFAOYSA-N 2-bromocyclopentan-1-one Chemical class BrC1CCCC1=O KZBPPOPPFUDSOP-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- OWAQXCQNWNJICI-UHFFFAOYSA-N benzene;chloroform Chemical compound ClC(Cl)Cl.C1=CC=CC=C1 OWAQXCQNWNJICI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 1
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS631171A CS153670B1 (enExample) | 1971-09-03 | 1971-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2232349A1 true DE2232349A1 (de) | 1973-03-08 |
Family
ID=5409856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2232349A Withdrawn DE2232349A1 (de) | 1971-09-03 | 1972-07-01 | Verfahren zur herstellung von 2-/ omega-alkoxycarbonylalkyl/-2-cyklopenten1-onen |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH568953A5 (enExample) |
| CS (1) | CS153670B1 (enExample) |
| DE (1) | DE2232349A1 (enExample) |
| IT (1) | IT1034027B (enExample) |
-
1971
- 1971-09-03 CS CS631171A patent/CS153670B1/cs unknown
-
1972
- 1972-07-01 DE DE2232349A patent/DE2232349A1/de not_active Withdrawn
- 1972-07-12 IT IT26922/72A patent/IT1034027B/it active
- 1972-08-03 CH CH1149172A patent/CH568953A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1034027B (it) | 1979-09-10 |
| CS153670B1 (enExample) | 1974-03-29 |
| CH568953A5 (enExample) | 1975-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2337813C3 (de) | Verfahren zur Herstellung von Monoacetalen aromatischer 1,2-Diketone | |
| DE2008878B2 (de) | 3-Keto-l-cyclopentenylessigsäurealkylester und Verfahren zu ihrer Herstellung | |
| DE2458164A1 (de) | Verfahren zur herstellung von neuen heterocyclischen verbindungen | |
| DE2725712C2 (de) | Verfahren zur Reduktion von Cephalosporinsulfoxiden | |
| DE2753454A1 (de) | Quadratsaeureester | |
| DE2505106A1 (de) | Neue hydroaromatische verbindungen | |
| DE69410318T2 (de) | Verfahren zur Herstellung eines Chinonderivates und Zwischenprodukt bei dessen Herstellung | |
| DE2232349A1 (de) | Verfahren zur herstellung von 2-/ omega-alkoxycarbonylalkyl/-2-cyklopenten1-onen | |
| DE2759994C2 (de) | Ketale von 4-(1-Hydroxy-1-methylethyl)-3-cyclohexen-1-on und Verfahren zu ihrer Herstellung | |
| CH544058A (de) | Verfahren zur Herstellung von Polyfluoralkylestern von Fumarsäure und verwandten Säuren | |
| DE2839762C2 (enExample) | ||
| DE2717502A1 (de) | Cyclohexenderivate und verfahren zu deren herstellung | |
| US3147282A (en) | Preparation of griseofulvin and analogues thereof | |
| AT214437B (de) | Verfahren zur Herstellung von teilhydrierten Anthrazenderivaten | |
| DE1157606B (de) | Verfahren zur Herstellung von 9-cis-Vitamin A bzw. dessen Estern | |
| AT272541B (de) | Verfahren zur Herstellung von Benzindenen | |
| AT271753B (de) | Verfahren zur Herstellung von neuen desA-Steroiden | |
| DE2415062C3 (de) | Verfahren zur Herstellung von 2-Nitrobenzaldehyd | |
| DE1031800B (de) | Verfahren zur Herstellung von Abkoemmlingen des Dioxolans | |
| AT214909B (de) | Verfahren zur Herstellung von ungesättigten Ketonen | |
| DE2052781A1 (en) | Octadienine hydrocarbons - prepd by octeninol dehydration with copper sulphate | |
| DE1050763B (de) | Synthese von Vitamin-A-Säure und ihren Estern | |
| DE1138043B (de) | Verfahren zur Herstellung tetracyclischer Ketone | |
| DE1091115B (de) | Verfahren zur Herstellung von 3-Formylmethyl-4-methyl-8-alkoxy-1, 2, 3, 4-tetrahydronphthalin-1-onen | |
| DE4008223A1 (de) | Verfahren zur herstellung von ss-resorcylsaeurederivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |