JPH0118889B2 - - Google Patents
Info
- Publication number
- JPH0118889B2 JPH0118889B2 JP56064194A JP6419481A JPH0118889B2 JP H0118889 B2 JPH0118889 B2 JP H0118889B2 JP 56064194 A JP56064194 A JP 56064194A JP 6419481 A JP6419481 A JP 6419481A JP H0118889 B2 JPH0118889 B2 JP H0118889B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- general formula
- methyl
- oxoheptanoate
- oxygen
- 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.)
- Expired
Links
- -1 polymethylene group Polymers 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000003997 cyclic ketones Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000862 absorption spectrum Methods 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- BSBYQAYWPXHLPQ-UHFFFAOYSA-N methyl 6-oxoheptanoate Chemical compound COC(=O)CCCCC(C)=O BSBYQAYWPXHLPQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical group COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- XZHVCFDNYKALMK-UHFFFAOYSA-N propan-2-yl 6-oxoheptanoate Chemical compound O=C(CCCCC(=O)OC(C)C)C XZHVCFDNYKALMK-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DRXLXYYFEDZGSZ-UHFFFAOYSA-N 2,3-diphenylcyclohexan-1-one Chemical compound O=C1CCCC(C=2C=CC=CC=2)C1C1=CC=CC=C1 DRXLXYYFEDZGSZ-UHFFFAOYSA-N 0.000 description 1
- LUGFNAYTNQMMMY-UHFFFAOYSA-N 2,5-dimethylcyclohexan-1-one Chemical compound CC1CCC(C)C(=O)C1 LUGFNAYTNQMMMY-UHFFFAOYSA-N 0.000 description 1
- JHMUMWBKYPMOLI-UHFFFAOYSA-N 2,6-diphenylcyclohexan-1-one Chemical compound O=C1C(C=2C=CC=CC=2)CCCC1C1=CC=CC=C1 JHMUMWBKYPMOLI-UHFFFAOYSA-N 0.000 description 1
- QREZMNNBJZCNSK-UHFFFAOYSA-N 2-naphthalen-2-ylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=C(C=CC=C2)C2=C1 QREZMNNBJZCNSK-UHFFFAOYSA-N 0.000 description 1
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- HFLTZADIZWIVCK-UHFFFAOYSA-N methyl 2-methyl-6-oxoheptanoate Chemical compound COC(=O)C(C)CCCC(C)=O HFLTZADIZWIVCK-UHFFFAOYSA-N 0.000 description 1
- OTUAHKIVWGKYIU-UHFFFAOYSA-N methyl 3-methyl-6-oxoheptanoate Chemical compound COC(=O)CC(C)CCC(C)=O OTUAHKIVWGKYIU-UHFFFAOYSA-N 0.000 description 1
- FDNFXHCDOASWAY-UHFFFAOYSA-N methyl 6-oxohexanoate Chemical compound COC(=O)CCCCC=O FDNFXHCDOASWAY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DCXPBOFGQPCWJY-UHFFFAOYSA-N trisodium;iron(3+);hexacyanide Chemical compound [Na+].[Na+].[Na+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCXPBOFGQPCWJY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56064194A JPS57181039A (en) | 1981-04-30 | 1981-04-30 | Preparation of oxocarboxylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56064194A JPS57181039A (en) | 1981-04-30 | 1981-04-30 | Preparation of oxocarboxylic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57181039A JPS57181039A (en) | 1982-11-08 |
| JPH0118889B2 true JPH0118889B2 (en]) | 1989-04-07 |
Family
ID=13251009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56064194A Granted JPS57181039A (en) | 1981-04-30 | 1981-04-30 | Preparation of oxocarboxylic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57181039A (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4649217A (en) * | 1982-04-02 | 1987-03-10 | Mitsubishi Chemical Industries Limited | Process for producing oxocarboxylic acids |
| JP5026833B2 (ja) * | 2006-03-28 | 2012-09-19 | 住友化学株式会社 | 光学活性（ｓ）−７−ヒドロキシ−６−メチルヘプタン−２−オンおよびその前駆体の製造方法 |
| WO2007114199A1 (ja) * | 2006-03-28 | 2007-10-11 | Sumitomo Chemical Company, Limited | 光学活性（ｓ）－７－ヒドロキシ－６－メチルヘプタン－２－オンおよびその前駆体の製造方法 |
-
1981
- 1981-04-30 JP JP56064194A patent/JPS57181039A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57181039A (en) | 1982-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0022162B1 (en) | Process for producing disubstituted 4-hydroxycyclopentenones; monosubstituted cyclopentendiones and 4-hydroxycyclopentenones | |
| US3847993A (en) | Allylic oxidation of bicyclic hydrocarbons to alcohols and ketones | |
| US20140316149A1 (en) | Aldehyde-selective wacker-type oxidation of unbiased alkenes | |
| Ando et al. | Reactions of enolates with vinyl selenoxides and vinyl selenones. One-step synthesis of cyclopropylcarbonyl compounds. | |
| Nakano et al. | Selective oxidation of alcohol function in allylic alcohols to. alpha.,. beta.-unsaturated carbonyl compounds catalyzed by zirconocene complexes | |
| JPH07505405A (ja) | スクラレオリドの製法 | |
| JPH0118889B2 (en]) | ||
| DE69402484T2 (de) | Verfahren zur Herstellung von Naphthochinonen sowie Zwischenprodukte bei deren Herstellung | |
| US4301084A (en) | Process for the preparation of carboxylic acid esters of β-formyl-crotyl alcohol by an allyl rearrangement | |
| US4181683A (en) | 1,7-Octadien-3-one and process for preparing the same | |
| Shimizu et al. | One-step oxidation of olefins into. ALPHA.-phenylseleno carbonyl compounds. | |
| Tamura et al. | Selective base-catalyzed rearrangement of epoxides into ketones. Application to. gamma.-keto sulfide synthesis | |
| JPH07103095B2 (ja) | ビタミンａアルデヒドの製造方法 | |
| US3914291A (en) | Process for splitting cycloaliphatic hydroperoxides | |
| JPH05286902A (ja) | α−クロロ−β−ケトエステル誘導体の製造方法 | |
| JP3529876B2 (ja) | ３−メチル−３−メトキシブタン酸。 | |
| US4085274A (en) | Process for preparing 4-oxopentadecanedioic acid | |
| JPH0832647B2 (ja) | １級アルコールからアルデヒドの製造法 | |
| JPS5852247A (ja) | オキソカルボン酸エステルの製造法 | |
| JPH0564944B2 (en]) | ||
| JP3946363B2 (ja) | カロテノイド類およびその製造方法 | |
| US4235785A (en) | 4-Acetyl-2-alkoxy-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane | |
| EP0008951B1 (en) | Steroid intermediate, method for production thereof, and method for producing another steroid intermediate therefrom | |
| JP2845607B2 (ja) | カルボニル基含有化合物の製造方法 | |
| JP4516831B2 (ja) | シス−ジャスモンの製造方法 |