CS203002B2 - Process for preparing alpha-diol-gamma-dioxocompounds - Google Patents
Process for preparing alpha-diol-gamma-dioxocompounds Download PDFInfo
- Publication number
- CS203002B2 CS203002B2 CS754025A CS402575A CS203002B2 CS 203002 B2 CS203002 B2 CS 203002B2 CS 754025 A CS754025 A CS 754025A CS 402575 A CS402575 A CS 402575A CS 203002 B2 CS203002 B2 CS 203002B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- diol
- solvent
- addition
- osmium tetroxide
- dioxocompounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 alkaline earth metal chlorate Chemical class 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract description 5
- 239000012285 osmium tetroxide Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 3
- 239000000284 extract Substances 0.000 abstract description 3
- 239000007858 starting material Substances 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 1
- 238000011010 flushing procedure Methods 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FJSKXQVRKZTKSI-UHFFFAOYSA-N 2,3-dimethylfuran Chemical compound CC=1C=COC=1C FJSKXQVRKZTKSI-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- HFIRJGXTWIQWEX-UHFFFAOYSA-N 2-n,5-n-dimethylfuran-2,5-diamine Chemical compound CNC1=CC=C(NC)O1 HFIRJGXTWIQWEX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-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
- 150000001224 Uranium Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000487 osmium oxide Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- JIWAALDUIFCBLV-UHFFFAOYSA-N oxoosmium Chemical compound [Os]=O JIWAALDUIFCBLV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23896/74A IT1014988B (it) | 1974-06-12 | 1974-06-12 | Processo per la preparazione di alfa diol gamma diosso composti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203002B2 true CS203002B2 (en) | 1981-02-27 |
Family
ID=11210711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS754025A CS203002B2 (en) | 1974-06-12 | 1975-06-09 | Process for preparing alpha-diol-gamma-dioxocompounds |
Country Status (18)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3067027D1 (en) * | 1980-01-11 | 1984-04-19 | Ici Plc | Process for the preparation of 1,4-dialkylbut-2-ene-1,4-diones |
| JPH0268150U (enrdf_load_stackoverflow) * | 1988-11-10 | 1990-05-23 |
-
1974
- 1974-06-12 IT IT23896/74A patent/IT1014988B/it active
-
1975
- 1975-05-23 YU YU01323/75A patent/YU132375A/xx unknown
- 1975-05-28 ZA ZA00753469A patent/ZA753469B/xx unknown
- 1975-06-05 FR FR7517602A patent/FR2279708A1/fr active Granted
- 1975-06-09 CS CS754025A patent/CS203002B2/cs unknown
- 1975-06-10 LU LU72706A patent/LU72706A1/xx unknown
- 1975-06-11 CA CA229,050A patent/CA1039749A/en not_active Expired
- 1975-06-11 NO NO752080A patent/NO141512C/no unknown
- 1975-06-11 CH CH755775A patent/CH605521A5/xx not_active IP Right Cessation
- 1975-06-11 DK DK264675A patent/DK264675A/da not_active Application Discontinuation
- 1975-06-11 IL IL47459A patent/IL47459A/xx unknown
- 1975-06-11 BE BE157224A patent/BE830109A/xx not_active IP Right Cessation
- 1975-06-11 HU HU75SA00002801A patent/HU172080B/hu unknown
- 1975-06-12 DD DD186609A patent/DD118069A5/xx unknown
- 1975-06-12 NL NL7507042A patent/NL7507042A/xx not_active Application Discontinuation
- 1975-06-12 JP JP50070241A patent/JPS5839137B2/ja not_active Expired
- 1975-06-12 GB GB25278/75A patent/GB1505667A/en not_active Expired
- 1975-06-12 SE SE7506763A patent/SE422199B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1014988B (it) | 1977-04-30 |
| NO141512B (no) | 1979-12-17 |
| BE830109A (fr) | 1975-10-01 |
| HU172080B (hu) | 1978-05-28 |
| GB1505667A (en) | 1978-03-30 |
| AU8145675A (en) | 1976-11-25 |
| JPS5111701A (en) | 1976-01-30 |
| IL47459A0 (en) | 1975-12-31 |
| ZA753469B (en) | 1976-05-26 |
| JPS5839137B2 (ja) | 1983-08-27 |
| DE2526050A1 (de) | 1975-12-18 |
| CA1039749A (en) | 1978-10-03 |
| FR2279708A1 (fr) | 1976-02-20 |
| NO141512C (no) | 1980-03-26 |
| IL47459A (en) | 1979-01-31 |
| DK264675A (da) | 1975-12-13 |
| NO752080L (enrdf_load_stackoverflow) | 1975-12-15 |
| DD118069A5 (enrdf_load_stackoverflow) | 1976-02-12 |
| LU72706A1 (enrdf_load_stackoverflow) | 1975-10-08 |
| DE2526050B2 (de) | 1977-04-21 |
| NL7507042A (nl) | 1975-12-16 |
| CH605521A5 (enrdf_load_stackoverflow) | 1978-09-29 |
| SE7506763L (sv) | 1975-12-15 |
| YU132375A (en) | 1982-02-28 |
| SE422199B (sv) | 1982-02-22 |
| FR2279708B1 (enrdf_load_stackoverflow) | 1978-05-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Boeckman Jr et al. | Cyclic vinyl ether carbanions—II: Preparation and applications to the synthesis of carbonyl compounds | |
| Rigby et al. | Total synthesis of guaianolides:(.+-.)-dehydrocostus lactone and (.+-.)-estafiatin | |
| FR2719046A1 (fr) | Procédé de préparation du ginkgolide B à partir du ginkgolide C. | |
| BE1003843A4 (fr) | Procede stereospecifique pour la preparation des enantiomeres de la furo (3,4-c) pyridine et composes ainsi obtenus. | |
| CS203002B2 (en) | Process for preparing alpha-diol-gamma-dioxocompounds | |
| Denmark et al. | Intramolecular [4+ 2] cycloadditions of nitrosoalkenes with olefins | |
| EP0171320B1 (fr) | Procédé de préparation de composés insaturés chlorés en alpha de deux groupements électroattracteurs en position bêta | |
| Hoppe et al. | A synthesis of bufalin from deoxycholic acid | |
| FR2489335A1 (enrdf_load_stackoverflow) | ||
| CS212221B2 (en) | Method of making the (+) 3a, 7a-trans-4-/7,7-/ethylenedioxy /-oxooktyl/-7a beta-methylperhydroindane-1,5-dion | |
| Bellesia et al. | The base-catalyzed cyclization of 10-oxocitral synthesis of chrysomelidal and dehydroiridodial | |
| JPS629098B2 (enrdf_load_stackoverflow) | ||
| EP0466583B1 (fr) | Procédé de préparation de la diméthyl-2,5 hydroxy-4 (2H)furanone-3 | |
| Li et al. | A CONVERGENT SYNTHESIS OF (±)-SARCOPHYTOL-A BENZYL ETHER | |
| CS196274B2 (en) | Method of producing diol-dione compounds | |
| FR2826005A1 (fr) | Synthese totale de la galanthamine, de ses analogues et de ses derives | |
| EP0012390A2 (fr) | Procédé pour la préparation de la muscone et composés pyranniques intermédiaires | |
| WO2024032799A1 (en) | Preparation Method of Tetrodotoxin and its Analog | |
| Nitta et al. | 1, 3-Dipolar cycloaddition reactions of 6-methylenetricyclo (3.2. 1.02, 7) oct-3-en-8-one and its related compounds. | |
| Meyer et al. | Reaction of nitrenes with strained olefins. Preparation and reactions of some 6‐azabicyclo [3.1. 0] hexanes | |
| Tomioka et al. | Nucleophilic cleavage reactions of cyclic and acyclic. alpha.-diazo-. beta.-ketophosphoryl compounds | |
| US4173707A (en) | Cyclopentanol derivatives | |
| JPH01319451A (ja) | ホルミルシクロプロパンの製法 | |
| JPS61171450A (ja) | シス‐ジヤスモンの製法 | |
| Arjona et al. | Chemo-and stereoselective functionalization of 7-oxabicyclo [2.2. 1] hept-5-en-2-one derivatives with the system trichloroacetyl chloride/Zn (Cu) 1 |