DE2313504A1 - Verfahren zur herstellung von cyclopentenonderivaten - Google Patents
Verfahren zur herstellung von cyclopentenonderivatenInfo
- Publication number
- DE2313504A1 DE2313504A1 DE2313504A DE2313504A DE2313504A1 DE 2313504 A1 DE2313504 A1 DE 2313504A1 DE 2313504 A DE2313504 A DE 2313504A DE 2313504 A DE2313504 A DE 2313504A DE 2313504 A1 DE2313504 A1 DE 2313504A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclopenten
- methyl
- solution
- water
- hydroxide solution
- 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 17
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 title description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 14
- CHCCBPDEADMNCI-UHFFFAOYSA-N 3-Methyl-2-cyclopenten-1-one Chemical compound CC1=CC(=O)CC1 CHCCBPDEADMNCI-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- NDTORNYEOXLIFZ-UHFFFAOYSA-N 1-methyl-6-oxabicyclo[3.1.0]hexan-4-one Chemical compound C1CC(=O)C2OC21C NDTORNYEOXLIFZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH513472A CH566953A5 (US20080293856A1-20081127-C00150.png) | 1972-04-07 | 1972-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2313504A1 true DE2313504A1 (de) | 1973-10-11 |
Family
ID=4288508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2313504A Pending DE2313504A1 (de) | 1972-04-07 | 1973-03-19 | Verfahren zur herstellung von cyclopentenonderivaten |
Country Status (10)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0621253A2 (en) * | 1993-02-11 | 1994-10-26 | Albemarle Corporation | Process for preparing cyclopentenones |
| US5856541A (en) * | 1995-02-17 | 1999-01-05 | Witco Gmbh | Process for preparing 1 3-disubstituted cyclopentadienyl ligands and transition metal complexes thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52122344A (en) * | 1976-04-05 | 1977-10-14 | Tatsuya Shiyouno | Process for manufacture of cyclopentenone derivatives |
| US4168280A (en) * | 1978-05-19 | 1979-09-18 | El Paso Products Company | Method for synthesis of 2-hydroxy-3-methyl cyclopent-2-ene-1-one |
| EP0245315B1 (de) * | 1985-11-20 | 1990-04-11 | L. GIVAUDAN & CIE Société Anonyme | VERFAHREN ZUR HERSTELLUNG VON $g(a)-HYDROXYCARBONYLVERBINDUNGEN |
| US5763664A (en) * | 1995-12-01 | 1998-06-09 | Albemarle Corporation | Process for preparing cyclopentenones |
| CN104496781A (zh) * | 2014-12-12 | 2015-04-08 | 上海万香日化有限公司 | 一种烷基环戊烯醇酮的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2387587A (en) * | 1939-01-04 | 1945-10-23 | Hunsdiecker Heinz | Process of manufacturing cyclopentenone derivatives |
| US3591643A (en) * | 1968-02-28 | 1971-07-06 | Procter & Gamble | Process for the preparation of bicyclo hexane compounds and the novel compound demethyl-cis-sabinene hydrate |
-
1972
- 1972-04-07 CH CH513472A patent/CH566953A5/xx not_active IP Right Cessation
-
1973
- 1973-02-23 IT IT20789/73A patent/IT979425B/it active
- 1973-02-27 NL NL7302705A patent/NL7302705A/xx not_active Application Discontinuation
- 1973-03-19 DE DE2313504A patent/DE2313504A1/de active Pending
- 1973-03-21 BR BR731994A patent/BR7301994D0/pt unknown
- 1973-04-05 US US348443A patent/US3907896A/en not_active Expired - Lifetime
- 1973-04-05 JP JP48039113A patent/JPS497251A/ja active Pending
- 1973-04-06 GB GB1660773A patent/GB1376582A/en not_active Expired
- 1973-04-06 FR FR7312493A patent/FR2179232B1/fr not_active Expired
- 1973-04-06 ES ES413405A patent/ES413405A1/es not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0621253A2 (en) * | 1993-02-11 | 1994-10-26 | Albemarle Corporation | Process for preparing cyclopentenones |
| EP0621253A3 (en) * | 1993-02-11 | 1995-02-01 | Albemarle Corp | Process for the manufacture of cydopentenones. |
| US5856541A (en) * | 1995-02-17 | 1999-01-05 | Witco Gmbh | Process for preparing 1 3-disubstituted cyclopentadienyl ligands and transition metal complexes thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS497251A (US20080293856A1-20081127-C00150.png) | 1974-01-22 |
| NL7302705A (US20080293856A1-20081127-C00150.png) | 1973-10-09 |
| FR2179232A1 (US20080293856A1-20081127-C00150.png) | 1973-11-16 |
| BR7301994D0 (pt) | 1974-02-07 |
| GB1376582A (en) | 1974-12-04 |
| ES413405A1 (es) | 1976-01-16 |
| CH566953A5 (US20080293856A1-20081127-C00150.png) | 1975-09-30 |
| US3907896A (en) | 1975-09-23 |
| FR2179232B1 (US20080293856A1-20081127-C00150.png) | 1976-11-12 |
| IT979425B (it) | 1974-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |