CN108727161A - A kind of method that the efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenol - Google Patents
A kind of method that the efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenol Download PDFInfo
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- CN108727161A CN108727161A CN201810801327.7A CN201810801327A CN108727161A CN 108727161 A CN108727161 A CN 108727161A CN 201810801327 A CN201810801327 A CN 201810801327A CN 108727161 A CN108727161 A CN 108727161A
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- Prior art keywords
- boric acid
- phenyl boric
- efficient
- department
- hydroxylating
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 title claims abstract description 48
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000000640 hydroxylating effect Effects 0.000 title claims abstract description 19
- 229960001922 sodium perborate Drugs 0.000 claims abstract description 25
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- LXDRHVXMGDKBEK-UHFFFAOYSA-N [B].C1=CC=CC=C1 Chemical compound [B].C1=CC=CC=C1 LXDRHVXMGDKBEK-UHFFFAOYSA-N 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 239000007800 oxidant agent Substances 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 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 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- PEYVWSJAZONVQK-UHFFFAOYSA-N hydroperoxy(oxo)borane Chemical compound OOB=O PEYVWSJAZONVQK-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07C37/055—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 the substituted group being bound to oxygen, e.g. ether group
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
The invention discloses the methods that a kind of efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenols, and phenyl boric acid and sodium perborate are added into solvent, and in the case of alkalinity or acid or not doping, directly stirring can obtain phenol.The synthetic method of the present invention is succinctly efficient, using common sodium perborate as oxidant, does not need catalyst, can directly efficiently synthesize phenol under mild conditions.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenol
Method.
Background technology
Phenolic compound plays critically important effect in terms of preventing and treating various diseases.It is efficiently synthesized benzene
One of phenol organic chemistry vital task.Phenyl boric acid synthesizing phenol has had received widespread attention in organic synthesis.Phenyl boric acid is low
Poison, property stable in the air is high, can directly buy in the market, cheap.Phenyl boric acid one's own department or unit hydroxylating prepares phenol and generally adopts
Oxidant is oxygen and hydrogen peroxide [Appl.Catal.A Gen., 2013,466,60-67；Appl.Catal.A:Gen,
2018,562,58-66].Sodium perborate is a kind of ideal oxidant, has few by-product, high selectivity, cheap etc. excellent
Point, the extensive use in organic synthesis.Therefore, it is that one kind efficiently may be used to prepare phenol with sodium perborate for oxidizing phenyl boric acid
Capable method.In the one hydroxylated reaction system in step one's own department or unit of phenyl boric acid, it is typically necessary metallic catalyst
[Chin.J.Org.Chem.,2016,36,862-866；Tetrahedron Lett.,2017,58(45),4255-4259；
Tetrahedron Lett.,2017,58(12),1211-1215；J.Organomet.Chem., 2017,851,52-56], golden
The problems such as presence of metal catalyst improves cost, and there are metal losses.Therefore, a kind of phenyl boric acid of no catalyst is developed
The new method that efficient one's own department or unit hydroxylating prepares phenol is particularly important.
Invention content
It is above-mentioned to overcome the purpose of the present invention is to provide the method that a kind of efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenol
Defect of the existing technology uses phenyl boric acid and sodium perborate for raw material, directly efficiently produces under mild reaction conditions
Phenol, synthetic method of the invention is succinctly efficient, is not necessarily to catalyst, substitutes hydrogen peroxide and oxygen with sodium perborate, improves peace
Quan Xing improves reaction efficiency.
In order to achieve the above objectives, the present invention adopts the following technical scheme that：
Phenyl boric acid and sodium perborate are added into solvent for a kind of method that the efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenol,
And additive, separating-purifying obtains phenol after then carrying out heating stirring reaction.
Further, the molar ratio of the phenyl boric acid and sodium perborate is 3:(1~5).
Further, the molar ratio of the additive and phenyl boric acid is 1:(1~2).
Further, the heating stirring reaction temperature is 0 DEG C~60 DEG C, and the time of reaction is 3min~1h.
Further, the reaction is not necessarily to catalyst.
Further, the solvent is in water, methanol, ethyl alcohol, acetone, tetrahydrofuran, acetonitrile, dichloromethane, ether
Any one.
Further, into solvent plus after phenyl boric acid and sodium perborate and additive, the concentration of phenyl boric acid in a solvent
For 0.1~0.3 mol/L.
Compared with prior art, the present invention has technique effect beneficial below：
The present invention directly generates phenol using phenylboric acid, sodium perborate, three component of additive, with phenyl boric acid and perboric acid
Sodium is raw material, and hydroxyl is introduced by one's own department or unit hydroxylating, need not be reacted under severe conditions, and product is easily isolated, production
Rate is higher.This reaction mechanism is as shown in formula (1), formula (2)：
Specific implementation mode
Embodiments of the present invention are described in further detail below：
A kind of method preparing benzene method phenol using sodium perborate oxidation phenyl boric acid, phenylboric acid and mistake are added into solvent
Boratex and additive, wherein the molar ratio of phenyl boric acid and sodium perborate is 3:1~3:5, phenyl boric acid and additive rub
You are than being 1:1~1:2, then a concentration of 0.1~0.3 mol/L of phenyl boric acid in a solvent is added at 0 DEG C~60 DEG C
3min~1h is reacted in thermal agitation, and rear separating-purifying obtains phenol.Shown in reaction mechanism such as formula (3)：
The present invention is described in further detail with reference to embodiment：
Embodiment 1
The phenyl boric acid of 5mmol, 5mmol sodium perborate and 5mmol additive sodium bicarbonates are added to the anti-of 10mL water
It answers in device.At 25 DEG C, phenyl boric acid and sodium perborate are dissolved in water with weak base, are stirred to react 30min at a certain temperature, then
Reaction solution is acidified to pH3~4, is detached, it is 92.3% to obtain phenol yield.
Embodiment 2
The phenyl boric acid of 5mmol, 5mmol sodium perborate and 5mmol additive sodium bicarbonates are added to 10mL methanol
In reactor.At 25 DEG C, phenyl boric acid and sodium perborate dissolving in methyl alcohol, are stirred to react 30min, then will at a certain temperature
Reaction solution is acidified to pH3~4, separation, and it is 91.6% to obtain yield.
Embodiment 3
The phenyl boric acid of 5mmol, 4mmol sodium perborate are added in the reactor of 10mL water, at 25 DEG C, reaction
30min.Reaction solution is acidified to pH3~4 again, is detached, it is 74.1% to obtain yield.
Embodiment 4
The phenyl boric acid of 5mmol, 5mmol sodium perborate are added in the reactor of 10mL water, at 25 DEG C, reaction
30min.Reaction solution is acidified to pH3~4 again, is detached, it is 93.7% to obtain yield.
Embodiment 5
The phenyl boric acid of 5mmol, 5mmol sodium perborate are added in the reactor of 10mL water, at 35 DEG C, reaction
30min.Reaction solution is acidified to pH3~4 again, is detached, it is 92.0% to obtain yield.
Embodiment 6
The phenyl boric acid of 3mmol, 15mmol sodium perborate and 6mmol additive hydrochloric acid are added to 10mL tetrahydrofurans
In reactor.At 25 DEG C, phenyl boric acid, sodium perborate and dissolving with hydrochloric acid in methyl alcohol, 3min are stirred to react at a temperature of 0 DEG C,
Reaction solution is acidified to pH3~4 again, is detached, it is 87.1% to obtain yield.
Claims (10)
1. a kind of method that the efficient one's own department or unit hydroxylating of phenyl boric acid prepares phenol, which is characterized in that pass through sodium perborate Oxybenzene boron
Acid, in the presence of water the boronate of phenyl boric acid is oxidized to phenolic hydroxyl group obtains phenol.
2. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 1 prepares phenol, which is characterized in that institute
The molar ratio of the benzene boron and sodium perborate stated is 3：（1~5）.
3. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 1 prepares phenol, which is characterized in that also
Additive is added into reaction system, for enabling sodium perborate generate stable [HOOB (OH)3]-Ion.
4. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 3 prepares phenol, which is characterized in that institute
Additive is stated as alkaline matter or acidic materials, the molar ratio of additive capacity and phenyl boric acid is 1:（1~2）.
5. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 4 prepares phenol, which is characterized in that institute
It is one or more in acetic acid, hydrochloric acid to state acidic materials.
6. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 1 prepares phenol, which is characterized in that institute
It is sodium bicarbonate to state alkaline matter.
7. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 1 prepares phenol, which is characterized in that institute
It states sodium perborate to carry out in solvent presence with reacting for phenyl boric acid, used solvent is water, methanol, ethyl alcohol, acetone, tetrahydrochysene
It is one or more in furans, acetonitrile, dichloromethane, ether solvent.
8. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 7 prepares phenol, which is characterized in that benzene
A concentration of 0.1~0.3 mol/L of boric acid in a solvent.
9. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 1 prepares phenol, which is characterized in that institute
The no catalyst of reaction stated.
10. the method that the efficient one's own department or unit hydroxylating of a kind of phenyl boric acid according to claim 1 prepares phenol, which is characterized in that
The temperature of reaction is 0 DEG C~60 DEG C, and the time of reaction is 3min~1h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810801327.7A CN108727161B (en) | 2018-07-18 | 2018-07-18 | Method for preparing phenol by efficient in-situ hydroxylation of phenylboronic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810801327.7A CN108727161B (en) | 2018-07-18 | 2018-07-18 | Method for preparing phenol by efficient in-situ hydroxylation of phenylboronic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108727161A true CN108727161A (en) | 2018-11-02 |
| CN108727161B CN108727161B (en) | 2021-09-07 |
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|---|---|---|---|
| CN201810801327.7A Active CN108727161B (en) | 2018-07-18 | 2018-07-18 | Method for preparing phenol by efficient in-situ hydroxylation of phenylboronic acid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110591109A (en) * | 2019-09-29 | 2019-12-20 | 上海交通大学 | Carbon-carbon double bond bridged full-carbon skeleton two-dimensional conjugated organic framework material and preparation method thereof |
| CN110668921A (en) * | 2019-08-27 | 2020-01-10 | 温州大学 | Method for preparing alcohol and phenol by aerobic hydroxylation reaction of boric acid derivative under condition of no photocatalyst |
| CN111151296A (en) * | 2020-01-09 | 2020-05-15 | 临沂大学 | Magnetic material loaded rhodamine B catalyst, preparation method thereof and catalytic application thereof in phenol synthesis |
-
2018
- 2018-07-18 CN CN201810801327.7A patent/CN108727161B/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110668921A (en) * | 2019-08-27 | 2020-01-10 | 温州大学 | Method for preparing alcohol and phenol by aerobic hydroxylation reaction of boric acid derivative under condition of no photocatalyst |
| CN110591109A (en) * | 2019-09-29 | 2019-12-20 | 上海交通大学 | Carbon-carbon double bond bridged full-carbon skeleton two-dimensional conjugated organic framework material and preparation method thereof |
| CN110591109B (en) * | 2019-09-29 | 2021-09-24 | 上海交通大学 | Carbon-carbon double bond bridged full-carbon skeleton two-dimensional conjugated organic framework material and preparation method thereof |
| CN111151296A (en) * | 2020-01-09 | 2020-05-15 | 临沂大学 | Magnetic material loaded rhodamine B catalyst, preparation method thereof and catalytic application thereof in phenol synthesis |
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| CN108727161B (en) | 2021-09-07 |
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