CA1039749A - PROCESS FOR THE PREPARATION OF .alpha.-DIOL-.gamma.-DIOXO COMPOUNDS - Google Patents
PROCESS FOR THE PREPARATION OF .alpha.-DIOL-.gamma.-DIOXO COMPOUNDSInfo
- Publication number
- CA1039749A CA1039749A CA229,050A CA229050A CA1039749A CA 1039749 A CA1039749 A CA 1039749A CA 229050 A CA229050 A CA 229050A CA 1039749 A CA1039749 A CA 1039749A
- Authority
- CA
- Canada
- Prior art keywords
- diol
- preparation
- process according
- represent
- general formula
- 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 11
- 239000012285 osmium tetroxide Substances 0.000 claims abstract description 12
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims abstract description 12
- 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 5
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- -1 alkaline earth metal chlorate Chemical class 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 150000002240 furans Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000796 flavoring agent Substances 0.000 abstract description 2
- 235000019634 flavors Nutrition 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002304 perfume Substances 0.000 abstract 1
- 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
- 239000000758 substrate Substances 0.000 description 5
- FJSKXQVRKZTKSI-UHFFFAOYSA-N 2,3-dimethylfuran Chemical compound CC=1C=COC=1C FJSKXQVRKZTKSI-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 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
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation 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 |
|---|---|
| CA1039749A true CA1039749A (en) | 1978-10-03 |
Family
ID=11210711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,050A Expired CA1039749A (en) | 1974-06-12 | 1975-06-11 | PROCESS FOR THE PREPARATION OF .alpha.-DIOL-.gamma.-DIOXO COMPOUNDS |
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 |
| FR2279708A1 (fr) | 1976-02-20 |
| NO141512C (no) | 1980-03-26 |
| IL47459A (en) | 1979-01-31 |
| CS203002B2 (en) | 1981-02-27 |
| 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 |
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