CH678056A5 - - Google Patents
Download PDFInfo
- Publication number
- CH678056A5 CH678056A5 CH207089A CH207089A CH678056A5 CH 678056 A5 CH678056 A5 CH 678056A5 CH 207089 A CH207089 A CH 207089A CH 207089 A CH207089 A CH 207089A CH 678056 A5 CH678056 A5 CH 678056A5
- Authority
- CH
- Switzerland
- Prior art keywords
- decomposition
- water
- hydroquinones
- diazonium salts
- diazonium salt
- Prior art date
Links
- 239000012954 diazonium Substances 0.000 claims description 19
- 150000001989 diazonium salts Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BXJGUBZTZWCMEX-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diol Chemical compound CC1=C(C)C(O)=CC=C1O BXJGUBZTZWCMEX-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl hydroquinones Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- UBKPLLYABUUFCE-UHFFFAOYSA-N 4-amino-2,3-dimethylphenol Chemical compound CC1=C(C)C(O)=CC=C1N UBKPLLYABUUFCE-UHFFFAOYSA-N 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-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
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19883818696 DE3818696C1 (en) | 1988-06-01 | 1988-06-01 | Process for the preparation of hydroquinone and its alkyl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH678056A5 true CH678056A5 (enrdf_load_stackoverflow) | 1991-07-31 |
Family
ID=6355649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207089A CH678056A5 (enrdf_load_stackoverflow) | 1988-06-01 | 1989-06-01 |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH678056A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3818696C1 (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2471530B1 (en) | 2005-06-01 | 2017-01-11 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| PL1933821T3 (pl) | 2005-09-15 | 2021-01-11 | Ptc Therapeutics, Inc. | Warianty łańcucha końcowego środków terapeutycznych o aktywności redoks do leczenia chorób mitochondrialnych i innych stanów oraz do modulacji biomarkerów energetycznych |
| EP1986636B1 (en) | 2006-02-22 | 2013-04-24 | Edison Pharmaceuticals, Inc. | Phenol and 1,4-benzoquinone derivatives for use in the treatment of mitochondrial diseases |
| EP3827815B1 (en) | 2008-09-10 | 2023-09-06 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| US10703701B2 (en) | 2015-12-17 | 2020-07-07 | Ptc Therapeutics, Inc. | Fluoroalkyl, fluoroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
-
1988
- 1988-06-01 DE DE19883818696 patent/DE3818696C1/de not_active Expired
-
1989
- 1989-06-01 CH CH207089A patent/CH678056A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3818696C1 (en) | 1989-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69021455T2 (de) | Verfahren zur Herstellung von Ascorbinsäure. | |
| DE2708468C3 (de) | Verfahren zur Herstellung von N, N'-Alkylen-bis-tetrabromophthalimiden | |
| DE2754017B1 (de) | Verfahren zum Herstellen eines Alkylen- oder Zykloalkylendiammoniumbis-Tetrahalophthalimides | |
| DE3818696C1 (en) | Process for the preparation of hydroquinone and its alkyl derivatives | |
| DE3308922A1 (de) | Verfahren zur herstellung von fettsaeureestern der ascorbinsaeure | |
| EP0013956B1 (de) | Verfahren zur Herstellung von Alkandiol-bis-aminobenzoesäureestern | |
| DE2627867A1 (de) | Verfahren zur herstellung von 2-hydroxybenzanthron und derivaten desselben sowie 2-hydroxybenzanthronderivate | |
| CH632731A5 (de) | Verfahren zur herstellung von alkoxy-substituierten polycyclischen aromatischen verbindungen. | |
| DE69706933T2 (de) | Verfahren zur Reinigung von 1,1,1-Tris(4-Hydroxyphenyl)alkanen | |
| EP0166684B1 (de) | Verfahren zur Herstellung von Hydroxyaromaten | |
| DE1965384A1 (de) | Verfahren zur Herstellung von p-Nitroso- und p-Nitrophenolen | |
| EP0341594B1 (de) | Verfahren zur Herstellung eines Addukts aus 2-Hydroxy-naphthalin-6-carbonsäure und 1,4-Dioxan und dessen Verwendung | |
| EP0279437B1 (de) | Verfahren zur Herstellung eines blauen anthrachinoiden Dispersionsfarbstoffs | |
| DE952629C (de) | Verfahren zur Herstellung aromatischer Oxyaldehyde | |
| CH407096A (de) | Verfahren zur Herstellung von aromatischen Diisothiocyanaten | |
| DE2413189C2 (de) | Verfahren zur Herstellung von Benzohydrochinonen | |
| DE3117321C2 (de) | Verfahren zur Herstellung von hochreinem Tolylthioharnstoff | |
| DD201680A5 (de) | Verfahren zur herstellung von apovincaminsaeureestern | |
| DE2231157A1 (de) | Verfahren zur nitrierung von phenolverbindungen | |
| DE3500029A1 (de) | Anthracyclinester | |
| DE3022783A1 (de) | Verfahren zur herstellung von 4-acylamido-2-nitro-1-alkoxybenzol-verbindungen | |
| CH683841A5 (de) | Verfahren zum Reinigen von roher 4,4'-Diamino-1,1'-dianthrachinonyl-3,3'-disulfonsäure und ihren Salzen. | |
| DE1670535A1 (de) | Verfahren zur Herstellung von Riboflavinphosphorsaeure | |
| CH646449A5 (de) | Faerbestabile modifikation eines monoazofarbstoffs sowie dessen herstellung. | |
| DD268964A1 (de) | Verfahren zur herstellung roter bis blauer biskationischer farbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |