GB1426769A - Process for the production of hydroquinone derivatives - Google Patents
Process for the production of hydroquinone derivativesInfo
- Publication number
- GB1426769A GB1426769A GB5583673A GB5583673A GB1426769A GB 1426769 A GB1426769 A GB 1426769A GB 5583673 A GB5583673 A GB 5583673A GB 5583673 A GB5583673 A GB 5583673A GB 1426769 A GB1426769 A GB 1426769A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diacetate
- mixture
- formula
- dihydrovitamin
- precursors
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 229930003448 Vitamin K Natural products 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- 235000019168 vitamin K Nutrition 0.000 abstract 2
- 239000011712 vitamin K Substances 0.000 abstract 2
- 150000003721 vitamin K derivatives Chemical class 0.000 abstract 2
- 229940046010 vitamin k Drugs 0.000 abstract 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- BUFJIHPUGZHTHL-NKFFZRIASA-N phyllohydroquinone Chemical compound C1=CC=CC2=C(O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(O)=C21 BUFJIHPUGZHTHL-NKFFZRIASA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1426769 Vitamin K precursors EISAI CO Ltd 3 Dec 1973 [4 Dec 1972 28 Sept 1973] 55836/73 Addition to 1424004 Heading C2V In a process for preparing vitamin K precursors of formula where R<SP>1</SP> and R<SP>2</SP> are methoxy groups or with the carbon atoms to which they are attached, constitute a benzene ring, A and B are hydrogen atoms or together form a direct bond and n is 0 or 1 to 9, by condensing a 2-halo-3-methyl-1,4- hydroquinone diacetate of formula where X is halogen, with an allyl halonickel #- complex of formula the condensation being carried out in a mixture of a solvent amide and a non-polar solvent to improve the proportion of trans isomer in the mixture of isomers obtained. In examples there are prepared dihydrovitamin K 1 diacetate, dihydrovitamin K 2(20) diacetate in mixtures of benzene and dimethylformamide and 2,3- dimethoxy - 5 - methyl - 6 - decaprenylhydroquinone diacetate in a mixture of n-hexane and dimethylacetamide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12067072A JPS5217025B2 (en) | 1972-12-04 | 1972-12-04 | |
| JP10853073A JPS5058021A (en) | 1973-09-28 | 1973-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1426769A true GB1426769A (en) | 1976-03-03 |
Family
ID=26448387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5583673A Expired GB1426769A (en) | 1972-12-04 | 1973-12-03 | Process for the production of hydroquinone derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2360382C2 (en) |
| FR (1) | FR2208881B1 (en) |
| GB (1) | GB1426769A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7528210B2 (en) | 2006-03-30 | 2009-05-05 | Sabic Innovative Plastics Ip B.V. | Method of purification of dihydric phenols |
| US7541417B2 (en) | 2006-03-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Process for the purification of dihydric phenols |
| US20150031651A1 (en) * | 2012-03-02 | 2015-01-29 | Kappa Bioscience As | Prodrugs of vitamine k |
| WO2018081644A1 (en) * | 2016-10-28 | 2018-05-03 | Bioelectron Technology Corporation | Methods of analyzing p-hydroquinone levels and ratios |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0183042B1 (en) * | 1984-11-21 | 1989-10-11 | F. Hoffmann-La Roche Ag | Process for the preparation of hydrochinone derivatives |
-
1973
- 1973-12-03 GB GB5583673A patent/GB1426769A/en not_active Expired
- 1973-12-04 DE DE19732360382 patent/DE2360382C2/en not_active Expired
- 1973-12-04 FR FR7343282A patent/FR2208881B1/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7528210B2 (en) | 2006-03-30 | 2009-05-05 | Sabic Innovative Plastics Ip B.V. | Method of purification of dihydric phenols |
| US7541417B2 (en) | 2006-03-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Process for the purification of dihydric phenols |
| US20150031651A1 (en) * | 2012-03-02 | 2015-01-29 | Kappa Bioscience As | Prodrugs of vitamine k |
| US9512153B2 (en) * | 2012-03-02 | 2016-12-06 | Kappa Bioscience As | Prodrugs of vitamine K |
| US10159687B2 (en) | 2012-03-02 | 2018-12-25 | Kappa Bioscience As | Prodrugs of vitamin K |
| WO2018081644A1 (en) * | 2016-10-28 | 2018-05-03 | Bioelectron Technology Corporation | Methods of analyzing p-hydroquinone levels and ratios |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2208881B1 (en) | 1976-11-19 |
| DE2360382C2 (en) | 1982-12-02 |
| FR2208881A1 (en) | 1974-06-28 |
| DE2360382A1 (en) | 1974-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed |