CN105859562A - Preparation method of o-nitrobenzaldehyde - Google Patents
Preparation method of o-nitrobenzaldehyde Download PDFInfo
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- CN105859562A CN105859562A CN201610229774.0A CN201610229774A CN105859562A CN 105859562 A CN105859562 A CN 105859562A CN 201610229774 A CN201610229774 A CN 201610229774A CN 105859562 A CN105859562 A CN 105859562A
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- CN
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- Prior art keywords
- nitrobenzene
- formyl
- benzoquinone
- preparation
- product
- 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.)
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- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000000047 product Substances 0.000 claims abstract description 19
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000006227 byproduct Substances 0.000 claims abstract description 8
- 230000002829 reductive effect Effects 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims description 12
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 9
- YBOZRPPSBVIHGJ-UHFFFAOYSA-N 1-nitro-2-[2-(2-nitrophenyl)ethyl]benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CCC1=CC=CC=C1[N+]([O-])=O YBOZRPPSBVIHGJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004811 liquid chromatography Methods 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BBQDLDVSEDAYAA-AATRIKPKSA-N 2-nitrocinnamic acid Chemical class OC(=O)\C=C\C1=CC=CC=C1[N+]([O-])=O BBQDLDVSEDAYAA-AATRIKPKSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical group [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002351 wastewater Substances 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of o-nitrobenzaldehyde, which comprises the step of reacting 1, 2-di (o-nitrophenyl) ethane and 5-10 times of benzoquinone by mol weight for 4-8 hours at the temperature of 120-; the liquid chromatography tracks the reaction process, after the reaction is finished, the excessive benzoquinone and the byproduct hydroquinone are recovered under reduced pressure, and 150-degree/15 mmHg products are collected as target products. The method is simple, the by-products can be recycled, and the method has great industrial value.
Description
Technical field
The present invention relates to a kind of pharmaceutical-chemical intermediate, be specifically related to the preparation method of a kind of 1-Formyl-2-nitrobenzene.
Background technology
1-Formyl-2-nitrobenzene (ONBD) is important medicine intermediate and organic synthesis raw material, is used for producing treatment hypertension
Medicine nifedipine, ortho-nitrophenyl vinyl and o-nitrocinnamic acid series products and the synthesis of quinoline ring class medicine, it is possible to
It is used as the important source material of synthesis plant growth regulator.Its synthetic method mainly has:
1, with ortho-methylnitrobenzene as raw material, first in the acetum of acetic anhydride, adjacent nitrobenzyl is prepared with chromic anhydride oxidation ortho-methylnitrobenzene
Fork diacetate esters intermediate, then hydrolyze through dilute sulfuric acid, vapor distillation obtains 1-Formyl-2-nitrobenzene, and its synthetic route is as follows:
The 1-Formyl-2-nitrobenzene purity that the method obtains is high, but consumes substantial amounts of acetic anhydride and acetic acid, and obtains chromate waste water, pollutes
Environment, is difficult to administer.
2, with benzaldehyde as raw material, the most under cryogenic, in the mixed liquor of acetic anhydride and concentrated sulphuric acid, the acetic anhydride of benzaldehyde is dripped
Solution, prepares intermediate benzyl diacetate esters again, then obtains adjacent nitrobenzyl diacetate esters again and to nitro through the nitrification of fuming nitric aicd
The yellow block mixture of benzyl diacetate esters again, is eventually adding aqueous sodium carbonate, add pyrohydrolysis prepare 1-Formyl-2-nitrobenzene and
Paranitrobenzaldehyde, its synthetic route is as follows:
The method obtains the mass ratio of 1-Formyl-2-nitrobenzene and paranitrobenzaldehyde and is about 3:2, and ortho para product separates ten
Point difficulty, this makes the yield of product 1-Formyl-2-nitrobenzene low and purity is low, is not suitable for industrialized production.
3, with nitro alcohol as raw material, oxygen or air are oxidant, and the complex of palladium is catalyst, at aqueous solution
In oxidized reaction prepare 1-Formyl-2-nitrobenzene, its synthetic route is as follows:
This route steps is short, and the selectivity of 1-Formyl-2-nitrobenzene is 100%, but yield only has 38%.
4, with o-Carboxynitrobenzene (as raw material, first obtain 2-(2-nitrobenzophenone)-2-imidazoline with reacting ethylenediamine, then
Obtaining 1-Formyl-2-nitrobenzene through reductive hydrolysis, its synthetic route is as follows:
The method synthesis technique is simple, mild condition, but product yield is low, is 49.2%.
5, with 1,2-bis-(O-Nitrophenylfluorone) ethylene is raw material, obtains o-Carboxynitrobenzene through smelly foster oxidation at-10 DEG C
And 1-Formyl-2-nitrobenzene, its synthetic route is as follows:
The method only needs single step reaction, and the most succinctly, product o-Carboxynitrobenzene (10) yield is 20%, 1-Formyl-2-nitrobenzene (1)
Yield is 75%, but by-product yield is higher, and separation is difficult to.
Summary of the invention
It is an object of the invention to: the preparation method of a kind of 1-Formyl-2-nitrobenzene is provided, utilize the raw material 1,2-of symmetrical configuration
Two (O-Nitrophenylfluorone) ethane and benzoquinone direct reaction prepare 1-Formyl-2-nitrobenzene, and the method is succinct, and by-product can recycle,
Great industrial value.
The technical solution of the present invention is: with 1, and 2-bis-(O-Nitrophenylfluorone) ethane is raw material, reacts with benzoquinone and obtains
Target product 1-Formyl-2-nitrobenzene, its reaction equation is as follows:
。
Its preparation process is specific as follows: by 1,2-bis-(O-Nitrophenylfluorone) ethane and the benzoquinone of its 5-10 times of mole,
React 4-8 hour in 120-150 DEG C；Liquid chromatograph follows the tracks of reaction process, after reaction terminates, and the benzoquinone of recovered under reduced pressure excess and pair
Product hydroquinone, collects 150-160 DEG C/15mmHg product, for target product.
Wherein, the mole of described benzoquinone is 1, and 6-8 times of 2-bis-(O-Nitrophenylfluorone) ethane mole is preferred.
The invention have the advantage that raw material 1,2-bis-(O-Nitrophenylfluorone) ethane can be raw material condensation system by adjacent nitro benzyl chloride
Standby, raw material is easy to get, and technique is simple, and the benzoquinone of excess and by-product hydroquinone can be to be utilized respectively after recovered under reduced pressure, separation, work
Industry Development volue is high.
Detailed description of the invention
Further illustrate the technical solution of the present invention below in conjunction with specific embodiment, these embodiments it is not intended that
It it is the restriction to technical scheme.
The analytical tool used in embodiment and equipment: gas chromatography mass spectrometry, MS5973N-GC6890N(U.S. Agilent is public
Department)；Nuclear magnetic resonance analyser, AVANCE DMX II I 400M(TMS internal standard, Bruker company)；High performance liquid chromatograph: Agilent
Technologies 1200 Series。
Embodiment 1: 136 grams of 1,2-bis-(O-Nitrophenylfluorone) ethane (0.50mol), 324 grams of benzoquinone (3.0mol) are added
In four mouthfuls of reaction bulbs of 1000 milliliters, after heating and melting, stirring and react 6 hours in 135 DEG C, high performance liquid chromatography follows the tracks of inspection
Survey；After reaction terminates, the benzoquinone of water pump recovered under reduced pressure excess and by-product hydroquinone, collect 150-160 DEG C/15mmHg product
147 grams, for target product 1-Formyl-2-nitrobenzene crude product, liquid content 94.5%, yield 92%；Obtain light by re-crystallizing in ethyl acetate
Yellow crystals 126.2 grams, mp42～44 DEG C, liquid content 99.1%, total recovery 82.8%.
Product structure is verified: IR (KBr, CHCl3): 3061, 2860, 2749, 1700, 1532, 1344 cm-1
;1H NMR (400 MHz): δ 10.36 (s, 1H), 8.09 (d, J = 8.0 Hz, 1H),7.92−7.90 (m,
1H), 7.81−7.74 (m, 2H);13C NMR (100 MHz): δ 188.2, 149.5, 134.2, 133.8, 131.4,
129.7, 124.6;MS: m/z 151, 121, 93, 76, 65 (100.0), 51。
Embodiment 2～8: the preparation condition experiment of 1-Formyl-2-nitrobenzene
136 grams of 1,2-bis-(O-Nitrophenylfluorone) ethane (0.50mol), a certain amount of benzoquinone are joined four mouthfuls of 1000 milliliters instead
Answer in bottle, after heating and melting, stir and react in uniform temperature, high performance liquid chromatography tracing detection；After reaction terminates, water pump reduces pressure
Reclaim benzoquinone and the by-product hydroquinone of excess, collect 150-160 DEG C/15mmHg product, for target product ortho-nitrophenyl first
Aldehyde crude product, liquid phase analysis content, calculated yield, result such as following table.
。
Claims (3)
1. the preparation method of 1-Formyl-2-nitrobenzene, is characterized in that: its preparation method is with 1,2-bis-(O-Nitrophenylfluorone) ethane
For raw material, reacting with benzoquinone and obtain target product 1-Formyl-2-nitrobenzene, its reaction equation is as follows:
。
The preparation method of 1-Formyl-2-nitrobenzene the most according to claim 1, is characterized in that its preparation process is as follows: by 1,
2-bis-(O-Nitrophenylfluorone) ethane and the benzoquinone of its 5-10 times of mole, react 4-8 hour in 120-150 DEG C；Liquid chromatograph with
Track reaction process, after reaction terminates, recovered under reduced pressure excess benzoquinone and by-product hydroquinone, collect 150-160 DEG C/15mmHg and produce
Product, for target product.
The preparation method of 1-Formyl-2-nitrobenzene the most according to claim 2, is characterized in that: the mole of described benzoquinone is
6-8 times of 1,2-bis-(O-Nitrophenylfluorone) ethane mole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610229774.0A CN105859562A (en) | 2016-04-14 | 2016-04-14 | Preparation method of o-nitrobenzaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610229774.0A CN105859562A (en) | 2016-04-14 | 2016-04-14 | Preparation method of o-nitrobenzaldehyde |
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| Publication Number | Publication Date |
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| CN105859562A true CN105859562A (en) | 2016-08-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610229774.0A Pending CN105859562A (en) | 2016-04-14 | 2016-04-14 | Preparation method of o-nitrobenzaldehyde |
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| Country | Link |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2041214B1 (en) * | 1992-02-20 | 1994-06-16 | Espanola Explosivos | Nitro-benzaldehyde intermediate prepn - from nitro-benzyl chloride(s) by dehydro-halogenation and dimerisation to di:nitro-stilbene cpds. followed by oxidn |
| CN102964191A (en) * | 2011-08-31 | 2013-03-13 | 中国科学院大连化学物理研究所 | Method for preparing aldehyde and ketone by alcohol oxidation |
| CN103539646A (en) * | 2013-10-14 | 2014-01-29 | 天津理工大学 | Method for preparing aldehyde or ketone by catalyzing oxygen to oxidize organic alcohol |
| CN104418753A (en) * | 2013-08-21 | 2015-03-18 | 南京理工大学 | Method for green-catalytically synthesizing nitrobenzaldehyde |
-
2016
- 2016-04-14 CN CN201610229774.0A patent/CN105859562A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2041214B1 (en) * | 1992-02-20 | 1994-06-16 | Espanola Explosivos | Nitro-benzaldehyde intermediate prepn - from nitro-benzyl chloride(s) by dehydro-halogenation and dimerisation to di:nitro-stilbene cpds. followed by oxidn |
| CN102964191A (en) * | 2011-08-31 | 2013-03-13 | 中国科学院大连化学物理研究所 | Method for preparing aldehyde and ketone by alcohol oxidation |
| CN104418753A (en) * | 2013-08-21 | 2015-03-18 | 南京理工大学 | Method for green-catalytically synthesizing nitrobenzaldehyde |
| CN103539646A (en) * | 2013-10-14 | 2014-01-29 | 天津理工大学 | Method for preparing aldehyde or ketone by catalyzing oxygen to oxidize organic alcohol |
Non-Patent Citations (2)
| Title |
|---|
| LIPENG ZHOU等: "Electronic Effect of Substituent of Quinones on their Catalytic Performance in Hydrocarbons Oxidation", 《CATALYSIS LETTERS》 * |
| QIAOHONG ZHANG等: "Efficient metal-free aerobic oxidation of aromatic hydrocarbons utilizing aryl-tetrahalogenated N-hydroxyphthalimides and 1,4-diamino-2,3-dichloroanthraquinone", 《JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY 》 * |
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