JPS58167537A - ２，６，６−トリメチル−４−オキソ−２−シクロヘキセニリデンアセトアルデヒドの製造法 - Google Patents
２，６，６−トリメチル−４−オキソ−２−シクロヘキセニリデンアセトアルデヒドの製造法Info
- Publication number
- JPS58167537A JPS58167537A JP4994982A JP4994982A JPS58167537A JP S58167537 A JPS58167537 A JP S58167537A JP 4994982 A JP4994982 A JP 4994982A JP 4994982 A JP4994982 A JP 4994982A JP S58167537 A JPS58167537 A JP S58167537A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- trimethyl
- formula
- cyclohexen
- cyclohexenylidene
- 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.)
- Granted
Links
- FPAOLXCWXKGVFW-UHFFFAOYSA-N 2-(6,6-dimethyl-4-oxocyclohex-2-en-1-ylidene)propanal Chemical compound CC(C=O)=C1C=CC(CC1(C)C)=O FPAOLXCWXKGVFW-UHFFFAOYSA-N 0.000 title abstract 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims description 7
- HYSVSSHMLNFRAM-UHFFFAOYSA-N 2,3,4-trimethylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C(C)=C1C HYSVSSHMLNFRAM-UHFFFAOYSA-N 0.000 claims 1
- OFAAPEDMUSMWFE-UHFFFAOYSA-N 2-cyclohex-2-en-1-ylideneacetaldehyde Chemical compound O=CC=C1CCCC=C1 OFAAPEDMUSMWFE-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 239000002904 solvent Substances 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract 3
- CBQXHTWJSZXYSK-UHFFFAOYSA-N 4-(2-butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one Chemical compound CC=CC=C1C(C)=CC(=O)CC1(C)C CBQXHTWJSZXYSK-UHFFFAOYSA-N 0.000 abstract 1
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000208125 Nicotiana Species 0.000 description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- -1 etc. Natural products 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- LITOJWOHJIGMOG-UHFFFAOYSA-N CCCCC=C=CC=O Chemical compound CCCCC=C=CC=O LITOJWOHJIGMOG-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- BUIQRTDBPCHRIR-UHFFFAOYSA-L O[Cr](Cl)(=O)=O Chemical compound O[Cr](Cl)(=O)=O BUIQRTDBPCHRIR-UHFFFAOYSA-L 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-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
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4994982A JPS58167537A (ja) | 1982-03-30 | 1982-03-30 | ２，６，６−トリメチル−４−オキソ−２−シクロヘキセニリデンアセトアルデヒドの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4994982A JPS58167537A (ja) | 1982-03-30 | 1982-03-30 | ２，６，６−トリメチル−４−オキソ−２−シクロヘキセニリデンアセトアルデヒドの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58167537A true JPS58167537A (ja) | 1983-10-03 |
| JPH0153660B2 JPH0153660B2 (enrdf_load_stackoverflow) | 1989-11-15 |
Family
ID=12845276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4994982A Granted JPS58167537A (ja) | 1982-03-30 | 1982-03-30 | ２，６，６−トリメチル−４−オキソ−２−シクロヘキセニリデンアセトアルデヒドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58167537A (enrdf_load_stackoverflow) |
-
1982
- 1982-03-30 JP JP4994982A patent/JPS58167537A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0153660B2 (enrdf_load_stackoverflow) | 1989-11-15 |
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