CA1039750A - PROCESS FOR THE PREPARATION OF .alpha.-DIOL-.gamma.-DIOXO COMPOUNDS - Google Patents
PROCESS FOR THE PREPARATION OF .alpha.-DIOL-.gamma.-DIOXO COMPOUNDSInfo
- Publication number
- CA1039750A CA1039750A CA229,051A CA229051A CA1039750A CA 1039750 A CA1039750 A CA 1039750A CA 229051 A CA229051 A CA 229051A CA 1039750 A CA1039750 A CA 1039750A
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- diol
- process according
- osmium tetroxide
- represent
- 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
- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000012285 osmium tetroxide Substances 0.000 claims abstract description 15
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 3
- -1 alkaline earth metal chlorate Chemical class 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000007363 ring formation reaction Methods 0.000 abstract description 4
- 150000002240 furans Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000000796 flavoring agent Substances 0.000 abstract description 2
- 235000019634 flavors Nutrition 0.000 abstract description 2
- 239000002304 perfume Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- OTSKZNVDZOOHRX-ARJAWSKDSA-N (z)-hex-3-ene-2,5-dione Chemical compound CC(=O)\C=C/C(C)=O OTSKZNVDZOOHRX-ARJAWSKDSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- VVZVXSHVLWHVPG-UHFFFAOYSA-N hex-4-ene-2,3-dione Chemical compound CC=CC(=O)C(C)=O VVZVXSHVLWHVPG-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OTSKZNVDZOOHRX-UHFFFAOYSA-N (3E)-3-hexene-2,5-dione Natural products CC(=O)C=CC(C)=O OTSKZNVDZOOHRX-UHFFFAOYSA-N 0.000 description 1
- OTSKZNVDZOOHRX-ONEGZZNKSA-N (e)-hex-3-ene-2,5-dione Chemical compound CC(=O)\C=C\C(C)=O OTSKZNVDZOOHRX-ONEGZZNKSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- MVGLBXWFOSHCCP-UHFFFAOYSA-N chloroform;tetrachloromethane Chemical compound ClC(Cl)Cl.ClC(Cl)(Cl)Cl MVGLBXWFOSHCCP-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2389874A IT1014990B (it) | 1974-06-12 | 1974-06-12 | Procedimento per la preparazione di alfa diol gamma diosso composti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039750A true CA1039750A (en) | 1978-10-03 |
Family
ID=11210734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,051A Expired CA1039750A (en) | 1974-06-12 | 1975-06-11 | PROCESS FOR THE PREPARATION OF .alpha.-DIOL-.gamma.-DIOXO COMPOUNDS |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5111703A (enExample) |
| BE (1) | BE830111A (enExample) |
| CA (1) | CA1039750A (enExample) |
| CH (1) | CH605523A5 (enExample) |
| FR (1) | FR2274593A1 (enExample) |
| GB (1) | GB1470734A (enExample) |
| IT (1) | IT1014990B (enExample) |
| LU (1) | LU72707A1 (enExample) |
| NL (1) | NL7507039A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56148944A (en) * | 1980-03-15 | 1981-11-18 | Shiyuuichi Higuchi | Weft yarn sending nozzle of loom |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3488394A (en) * | 1966-05-11 | 1970-01-06 | Fmc Corp | Oxidation of olefinic compounds to glycols |
-
1974
- 1974-06-12 IT IT2389874A patent/IT1014990B/it active
-
1975
- 1975-06-05 FR FR7517604A patent/FR2274593A1/fr active Granted
- 1975-06-10 LU LU72707A patent/LU72707A1/xx unknown
- 1975-06-11 CH CH755975A patent/CH605523A5/xx not_active IP Right Cessation
- 1975-06-11 CA CA229,051A patent/CA1039750A/en not_active Expired
- 1975-06-11 BE BE157226A patent/BE830111A/xx not_active IP Right Cessation
- 1975-06-12 GB GB2528075A patent/GB1470734A/en not_active Expired
- 1975-06-12 JP JP7024375A patent/JPS5111703A/ja active Pending
- 1975-06-12 NL NL7507039A patent/NL7507039A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2274593A1 (fr) | 1976-01-09 |
| DE2525827B2 (de) | 1977-01-20 |
| JPS5111703A (en) | 1976-01-30 |
| BE830111A (fr) | 1975-10-01 |
| IT1014990B (it) | 1977-04-30 |
| FR2274593B1 (enExample) | 1977-07-08 |
| NL7507039A (nl) | 1975-12-16 |
| LU72707A1 (enExample) | 1975-10-08 |
| CH605523A5 (enExample) | 1978-09-29 |
| GB1470734A (en) | 1977-04-21 |
| DE2525827A1 (de) | 1975-12-18 |
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