NO831362L - Fremgangsmaate ved fremstilling av o-nitrobenzaldehyd. - Google Patents
Fremgangsmaate ved fremstilling av o-nitrobenzaldehyd.Info
- Publication number
- NO831362L NO831362L NO831362A NO831362A NO831362L NO 831362 L NO831362 L NO 831362L NO 831362 A NO831362 A NO 831362A NO 831362 A NO831362 A NO 831362A NO 831362 L NO831362 L NO 831362L
- Authority
- NO
- Norway
- Prior art keywords
- nitrobenzaldehyde
- formula
- oxidation
- hydrogen peroxide
- compound
- Prior art date
Links
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 18
- -1 enol salt Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 13
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000021736 acetylation Effects 0.000 claims description 2
- 238000006640 acetylation reaction Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 8
- CGCWRLDEYHZQCW-UHFFFAOYSA-N 2-nitrophenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1[N+]([O-])=O CGCWRLDEYHZQCW-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- DVPVPDZDPCZUEF-UHFFFAOYSA-N (2-nitrophenyl) 2-oxopropanoate Chemical compound CC(=O)C(=O)OC1=CC=CC=C1[N+]([O-])=O DVPVPDZDPCZUEF-UHFFFAOYSA-N 0.000 abstract 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000012071 phase Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KTTXUOADWOUYQV-UHFFFAOYSA-N (2-nitrophenyl)methyl formate Chemical compound [O-][N+](=O)C1=CC=CC=C1COC=O KTTXUOADWOUYQV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- AKWXORMMOJRIBI-UHFFFAOYSA-N ethyl 3-(2-nitrophenyl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=CC=C1[N+]([O-])=O AKWXORMMOJRIBI-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WMUZDBZPDLHUMW-UHFFFAOYSA-N (2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1[N+]([O-])=O WMUZDBZPDLHUMW-UHFFFAOYSA-N 0.000 description 1
- BWRBVBFLFQKBPT-UHFFFAOYSA-N (2-nitrophenyl)methanol Chemical compound OCC1=CC=CC=C1[N+]([O-])=O BWRBVBFLFQKBPT-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- HXBMIQJOSHZCFX-UHFFFAOYSA-N 1-(bromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CBr HXBMIQJOSHZCFX-UHFFFAOYSA-N 0.000 description 1
- HETXONIWLNSRGY-UHFFFAOYSA-N 1-(dibromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Br)Br HETXONIWLNSRGY-UHFFFAOYSA-N 0.000 description 1
- IREGSVSQCKFDNG-UHFFFAOYSA-N 1-(dichloromethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)Cl IREGSVSQCKFDNG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OHOKNZHGCGAZKX-UHFFFAOYSA-N ethyl 2-acetyloxy-3-(2-nitrophenyl)prop-2-enoate Chemical compound CCOC(=O)C(OC(C)=O)=CC1=CC=CC=C1[N+]([O-])=O OHOKNZHGCGAZKX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH235282 | 1982-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO831362L true NO831362L (no) | 1983-10-20 |
Family
ID=4231774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO831362A NO831362L (no) | 1982-04-19 | 1983-04-18 | Fremgangsmaate ved fremstilling av o-nitrobenzaldehyd. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4463195A (xx) |
| EP (1) | EP0092267B1 (xx) |
| JP (1) | JPS58189140A (xx) |
| AT (1) | ATE12630T1 (xx) |
| DE (1) | DE3360105D1 (xx) |
| DK (1) | DK165183A (xx) |
| FI (1) | FI831274L (xx) |
| IL (1) | IL68427A (xx) |
| NO (1) | NO831362L (xx) |
| ZA (1) | ZA832696B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE456577B (sv) * | 1984-06-13 | 1988-10-17 | Nobel Kemi Ab | Sett att framstella o- och p-nitrobensaldehyd |
| US5258544A (en) * | 1991-03-05 | 1993-11-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Synthesis of aldehydes useful in the preparations of HMG-CoA reductase inhibitors |
| DE4408007A1 (de) * | 1994-03-10 | 1995-09-14 | Bayer Ag | Verfahren zur Herstellung von 2-Nitrobenzaldehyden |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB190421047A (en) * | 1903-11-28 | 1904-11-24 | George Darzens | Manufacture of Certain Aldehydes and Intermediate Products. |
| US3287393A (en) * | 1963-04-22 | 1966-11-22 | Bofors Ab | Method of preparing 2-chloro-6-nitro-benzonitrile |
| EG11639A (en) * | 1974-03-28 | 1977-11-30 | Bayer Ag | Process for the preparation of 2-nitrobenzoldehyde |
| AR204859A1 (es) * | 1974-03-28 | 1976-03-05 | Bayer Ag | Procedimiento para la produccion de 2-nitrobenzaldehido |
| DE2808930A1 (de) * | 1978-03-02 | 1979-09-06 | Bayer Ag | Verfahren zur herstellung von 2-nitrobenzaldehyd |
-
1983
- 1983-04-08 AT AT83200498T patent/ATE12630T1/de not_active IP Right Cessation
- 1983-04-08 EP EP83200498A patent/EP0092267B1/en not_active Expired
- 1983-04-08 DE DE8383200498T patent/DE3360105D1/de not_active Expired
- 1983-04-14 US US06/484,842 patent/US4463195A/en not_active Expired - Fee Related
- 1983-04-15 DK DK165183A patent/DK165183A/da not_active Application Discontinuation
- 1983-04-15 FI FI831274A patent/FI831274L/fi not_active Application Discontinuation
- 1983-04-17 IL IL68427A patent/IL68427A/xx unknown
- 1983-04-18 ZA ZA832696A patent/ZA832696B/xx unknown
- 1983-04-18 NO NO831362A patent/NO831362L/no unknown
- 1983-04-19 JP JP58067911A patent/JPS58189140A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL68427A0 (en) | 1983-07-31 |
| DE3360105D1 (en) | 1985-05-15 |
| FI831274A0 (fi) | 1983-04-15 |
| EP0092267A1 (en) | 1983-10-26 |
| IL68427A (en) | 1985-12-31 |
| EP0092267B1 (en) | 1985-04-10 |
| DK165183A (da) | 1983-10-20 |
| JPS58189140A (ja) | 1983-11-04 |
| ZA832696B (en) | 1983-12-28 |
| DK165183D0 (da) | 1983-04-15 |
| ATE12630T1 (de) | 1985-04-15 |
| FI831274L (fi) | 1983-10-20 |
| US4463195A (en) | 1984-07-31 |
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