GB2387595B - Preparation of vicinal diols - Google Patents
Preparation of vicinal diolsInfo
- Publication number
- GB2387595B GB2387595B GB0307128A GB0307128A GB2387595B GB 2387595 B GB2387595 B GB 2387595B GB 0307128 A GB0307128 A GB 0307128A GB 0307128 A GB0307128 A GB 0307128A GB 2387595 B GB2387595 B GB 2387595B
- Authority
- GB
- United Kingdom
- Prior art keywords
- dhqd
- hypohalite
- diether
- vicinal diols
- compound used
- 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 - Fee Related
Links
- 150000002009 diols Chemical group 0.000 title abstract 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkaline earth metal hypochlorite Chemical class 0.000 abstract 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 abstract 2
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 2
- 150000002830 nitrogen compounds Chemical class 0.000 abstract 2
- 150000002908 osmium compounds Chemical class 0.000 abstract 2
- LJOQGZACKSYWCH-LHHVKLHASA-N (s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol Chemical compound C1=C(OC)C=C2C([C@H](O)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-LHHVKLHASA-N 0.000 abstract 1
- YUCBLVFHJWOYDN-HVLQGHBFSA-N 1,4-bis[(s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]phthalazine Chemical compound C1=C(OC)C=C2C([C@H](OC=3C4=CC=CC=C4C(O[C@H]([C@@H]4N5CC[C@H]([C@H](C5)CC)C4)C=4C5=CC(OC)=CC=C5N=CC=4)=NN=3)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 YUCBLVFHJWOYDN-HVLQGHBFSA-N 0.000 abstract 1
- SWKRDCRSJPRVNF-DOGDSVMGSA-N 4-[(s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-[6-[(s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]-2,5-diphenylpyrimidin-4-yl]oxymethyl]-6-methoxyquinoline Chemical compound O([C@H]([C@H]1C[C@@H]2CCN1C[C@@H]2CC)C=1C2=CC(OC)=CC=C2N=CC=1)C1=NC(C=2C=CC=CC=2)=NC(O[C@H]([C@@H]2N3CC[C@H]([C@H](C3)CC)C2)C=2C3=CC(OC)=CC=C3N=CC=2)=C1C1=CC=CC=C1 SWKRDCRSJPRVNF-DOGDSVMGSA-N 0.000 abstract 1
- LJOQGZACKSYWCH-AFHBHXEDSA-N Hydroquinidine Natural products C1=C(OC)C=C2C([C@@H](O)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-AFHBHXEDSA-N 0.000 abstract 1
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- DGODWNOPHMXOTR-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium;dihydrate Chemical compound O.O.[K+].[K+].[O-][Os]([O-])(=O)=O DGODWNOPHMXOTR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 229960000811 hydroquinidine Drugs 0.000 abstract 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing vicinal diols comprises the conversion of olefins in the presence of hypohalite, catalysts comprising at least one osmium compound, water and nitrogen compounds. The reaction mixture may further comprise an organic solvent, particular tert-butanol. The hypohalite is preferably an alkali metal or alkaline earth metal hypochlorite or hypobromite, especially sodium hypochlorite. The nitrogen compound used is preferably (DHQD)2PHAL (dihydroquinidine-1,4-phalazinediyl diether) or (DHQD)2Pyr (hydroquinidine(2,5 -diphenyl-4,6-pyrimidinediyl) diether). The osmium compound used is preferably potassium osmate dihydrate. The diols prepared may be used for preparing polymers, herbicides, fungicides, insecticides, pharmaceuticals and cosmetics or their precursors.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10213981A DE10213981A1 (en) | 2002-03-28 | 2002-03-28 | Process for the preparation of vicinal diols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB0307128D0 GB0307128D0 (en) | 2003-04-30 |
| GB2387595A GB2387595A (en) | 2003-10-22 |
| GB2387595B true GB2387595B (en) | 2005-07-27 |
Family
ID=7714241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0307128A Expired - Fee Related GB2387595B (en) | 2002-03-28 | 2003-03-27 | Preparation of vicinal diols |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE10213981A1 (en) |
| FR (1) | FR2839511A1 (en) |
| GB (1) | GB2387595B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3488394A (en) * | 1966-05-11 | 1970-01-06 | Fmc Corp | Oxidation of olefinic compounds to glycols |
| EP0077202A2 (en) * | 1981-10-09 | 1983-04-20 | Exxon Research And Engineering Company | Process for hydroxylating olefins using osmium-halogen compound catalysts |
| US5419817A (en) * | 1992-02-21 | 1995-05-30 | Sepracor Inc. | Electrocatalytic asymmetric dihydroxylation of olefinic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6573387B1 (en) * | 1997-03-21 | 2003-06-03 | The Scripps Research Institute | Synthesis of α,β-substituted amino amides, esters, and acids |
-
2002
- 2002-03-28 DE DE10213981A patent/DE10213981A1/en not_active Withdrawn
-
2003
- 2003-03-27 GB GB0307128A patent/GB2387595B/en not_active Expired - Fee Related
- 2003-03-28 FR FR0303847A patent/FR2839511A1/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3488394A (en) * | 1966-05-11 | 1970-01-06 | Fmc Corp | Oxidation of olefinic compounds to glycols |
| EP0077202A2 (en) * | 1981-10-09 | 1983-04-20 | Exxon Research And Engineering Company | Process for hydroxylating olefins using osmium-halogen compound catalysts |
| US5419817A (en) * | 1992-02-21 | 1995-05-30 | Sepracor Inc. | Electrocatalytic asymmetric dihydroxylation of olefinic compounds |
Non-Patent Citations (1)
| Title |
|---|
| Tetrahedron Letters Vol. 41, 2000, pages 5141-5145 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2387595A (en) | 2003-10-22 |
| FR2839511A1 (en) | 2003-11-14 |
| DE10213981A1 (en) | 2003-10-16 |
| GB0307128D0 (en) | 2003-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20080327 |