DE2016750A1 - Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionen - Google Patents
Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionenInfo
- Publication number
- DE2016750A1 DE2016750A1 DE19702016750 DE2016750A DE2016750A1 DE 2016750 A1 DE2016750 A1 DE 2016750A1 DE 19702016750 DE19702016750 DE 19702016750 DE 2016750 A DE2016750 A DE 2016750A DE 2016750 A1 DE2016750 A1 DE 2016750A1
- Authority
- DE
- Germany
- Prior art keywords
- dione
- oxobutyl
- general formula
- solvent
- ethyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 7
- 241000551547 Dione <red algae> Species 0.000 title description 2
- 150000001924 cycloalkanes Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- -1 3-oxobutyl Chemical group 0.000 claims description 10
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- ZQYLUOYVHHWICM-UHFFFAOYSA-N 2-butyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound C(CCC)C1(C(CCCC1=O)=O)CCC(C)=O ZQYLUOYVHHWICM-UHFFFAOYSA-N 0.000 claims 1
- JTRQSSRXYULBAA-UHFFFAOYSA-N 2-ethyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound CC(=O)CCC1(CC)C(=O)CCCC1=O JTRQSSRXYULBAA-UHFFFAOYSA-N 0.000 claims 1
- ZNVNGGMKNCURSF-UHFFFAOYSA-N 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound CC(=O)CCC1(C)C(=O)CCCC1=O ZNVNGGMKNCURSF-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- XNCNNDVCAUWAIT-UHFFFAOYSA-N Methyl heptanoate Chemical compound CCCCCCC(=O)OC XNCNNDVCAUWAIT-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HXZILEQYFQYQCE-UHFFFAOYSA-N 2-methylcyclopentane-1,3-dione Chemical compound CC1C(=O)CCC1=O HXZILEQYFQYQCE-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LDAOEWRCYIBKFV-UHFFFAOYSA-N 4-(1-methylcyclopentyl)butan-2-one Chemical compound CC(=O)CCC1(C)CCCC1 LDAOEWRCYIBKFV-UHFFFAOYSA-N 0.000 description 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 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
- 239000013543 active substance Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- IQQDLHGWGKEQDS-UHFFFAOYSA-N methyl hept-2-enoate Chemical compound CCCCC=CC(=O)OC IQQDLHGWGKEQDS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003128 pregnanes Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/395—Saturated compounds containing a keto group being part of a ring of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702016750 DE2016750A1 (de) | 1970-04-04 | 1970-04-04 | Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionen |
| ES388905A ES388905A1 (es) | 1970-04-04 | 1971-03-04 | Procedimiento para la preparacion de cicloalcan-1,3-dionas 2,2-disustituidas. |
| SU1628609A SU376933A1 (ru) | 1971-03-05 | Способ получения 2,2-дизаме1ценных циклоалкан-1,3- | |
| ZA711489A ZA711489B (en) | 1970-04-04 | 1971-03-08 | Process for the manufacture of 2,2-disubstituted cycloalkane-1,3-diones |
| CS1967A CS176154B2 (en:Method) | 1970-04-04 | 1971-03-18 | |
| IE407/71A IE35261B1 (en) | 1970-04-04 | 1971-03-30 | Process for the manufacture of 2,2-disubstituted cycloalkane-1,3-diones |
| IL36516A IL36516A (en) | 1970-04-04 | 1971-03-30 | Process for the manufacture of 2,2-disubstituted cycloalkane-1,3-diones |
| IT22604/71A IT1043837B (it) | 1970-04-04 | 1971-04-01 | Procedimento per preparare cicloal can 1 3 oioni bisostituiti in posizione 2 2 |
| BE765214A BE765214A (fr) | 1970-04-04 | 1971-04-02 | Cycloalkane-1,3-diones 2,2-disubstituees et leur procede de preparatio |
| US00113223A US3816536A (en) | 1970-04-04 | 1971-04-02 | 2-2-disubstituted cycloalkane-1,3-diones |
| PL1971147330A PL81640B1 (en:Method) | 1970-04-04 | 1971-04-02 | |
| AT283771A AT310140B (de) | 1970-04-04 | 1971-04-02 | Verfahren zur Herstellung von 2-Alkyl-2-(3'-oxoalkyl)-cycloalkan-1,3-dionen |
| FR7111700A FR2085844B1 (en:Method) | 1970-04-04 | 1971-04-02 | |
| NL7104561A NL7104561A (en:Method) | 1970-04-04 | 1971-04-05 | |
| GB2562571*A GB1351852A (en) | 1970-04-04 | 1971-04-19 | Process for the manufacture of 2,2,-disubstituted cycloalkane- 1,3-diones |
| DE20221711U DE20221711U1 (de) | 1970-04-04 | 2002-07-26 | Linse zum Einbau in eine Brillenfassung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702016750 DE2016750A1 (de) | 1970-04-04 | 1970-04-04 | Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2016750A1 true DE2016750A1 (de) | 1971-10-14 |
Family
ID=5767452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702016750 Pending DE2016750A1 (de) | 1970-04-04 | 1970-04-04 | Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3816536A (en:Method) |
| AT (1) | AT310140B (en:Method) |
| BE (1) | BE765214A (en:Method) |
| CS (1) | CS176154B2 (en:Method) |
| DE (1) | DE2016750A1 (en:Method) |
| ES (1) | ES388905A1 (en:Method) |
| FR (1) | FR2085844B1 (en:Method) |
| GB (1) | GB1351852A (en:Method) |
| IE (1) | IE35261B1 (en:Method) |
| IL (1) | IL36516A (en:Method) |
| IT (1) | IT1043837B (en:Method) |
| NL (1) | NL7104561A (en:Method) |
| PL (1) | PL81640B1 (en:Method) |
| ZA (1) | ZA711489B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659070A (en) * | 1995-02-02 | 1997-08-19 | Basf Aktiengesellschaft | Preparation of alkyl 5-oxo-6-heptenoates, and novel intermediate for the preparation thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975440A (en) * | 1970-01-21 | 1976-08-17 | Hoffmann-La Roche Inc. | Asymmetric synthesis of organic compounds |
| US4072716A (en) * | 1971-12-24 | 1978-02-07 | Schering Aktiengesellschaft | Bicycloalkane derivatives |
| US3972896A (en) * | 1973-05-24 | 1976-08-03 | Hoffmann-La Roche Inc. | Aryl ketals of polycyclic oxo compounds and processes |
| DE2516544A1 (de) * | 1975-04-14 | 1976-11-04 | Schering Ag | Verfahren zur herstellung von trans-decalin-derivaten |
| JPS5538315A (en) * | 1978-09-08 | 1980-03-17 | Takeda Chem Ind Ltd | Intermediate for synthesis of steroids and its preparation |
-
1970
- 1970-04-04 DE DE19702016750 patent/DE2016750A1/de active Pending
-
1971
- 1971-03-04 ES ES388905A patent/ES388905A1/es not_active Expired
- 1971-03-08 ZA ZA711489A patent/ZA711489B/xx unknown
- 1971-03-18 CS CS1967A patent/CS176154B2/cs unknown
- 1971-03-30 IL IL36516A patent/IL36516A/xx unknown
- 1971-03-30 IE IE407/71A patent/IE35261B1/xx unknown
- 1971-04-01 IT IT22604/71A patent/IT1043837B/it active
- 1971-04-02 PL PL1971147330A patent/PL81640B1/pl unknown
- 1971-04-02 AT AT283771A patent/AT310140B/de not_active IP Right Cessation
- 1971-04-02 FR FR7111700A patent/FR2085844B1/fr not_active Expired
- 1971-04-02 US US00113223A patent/US3816536A/en not_active Expired - Lifetime
- 1971-04-02 BE BE765214A patent/BE765214A/xx unknown
- 1971-04-05 NL NL7104561A patent/NL7104561A/xx unknown
- 1971-04-19 GB GB2562571*A patent/GB1351852A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659070A (en) * | 1995-02-02 | 1997-08-19 | Basf Aktiengesellschaft | Preparation of alkyl 5-oxo-6-heptenoates, and novel intermediate for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US3816536A (en) | 1974-06-11 |
| ZA711489B (en) | 1971-11-24 |
| IE35261L (en) | 1971-10-04 |
| GB1351852A (en) | 1974-05-01 |
| IL36516A (en) | 1975-10-15 |
| ES388905A1 (es) | 1973-06-01 |
| FR2085844A1 (en:Method) | 1971-12-31 |
| NL7104561A (en:Method) | 1971-10-06 |
| CS176154B2 (en:Method) | 1977-06-30 |
| IL36516A0 (en) | 1971-05-26 |
| SU376933A3 (en:Method) | 1973-04-05 |
| IT1043837B (it) | 1980-02-29 |
| PL81640B1 (en:Method) | 1975-08-30 |
| AT310140B (de) | 1973-09-25 |
| IE35261B1 (en) | 1975-12-24 |
| BE765214A (fr) | 1971-10-04 |
| FR2085844B1 (en:Method) | 1976-06-04 |
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