CN103242153A - Method for catalyzing preparation of benzoin from benzaldehyde by adopting imidazolium bicarbonate ionic liquid - Google Patents
Method for catalyzing preparation of benzoin from benzaldehyde by adopting imidazolium bicarbonate ionic liquid Download PDFInfo
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- CN103242153A CN103242153A CN2013101685266A CN201310168526A CN103242153A CN 103242153 A CN103242153 A CN 103242153A CN 2013101685266 A CN2013101685266 A CN 2013101685266A CN 201310168526 A CN201310168526 A CN 201310168526A CN 103242153 A CN103242153 A CN 103242153A
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- benzaldehyde
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- phenyl aldehyde
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000002608 ionic liquid Substances 0.000 title abstract description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title abstract 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 title abstract 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title abstract 4
- 244000028419 Styrax benzoin Species 0.000 title abstract 3
- 235000000126 Styrax benzoin Nutrition 0.000 title abstract 3
- 235000008411 Sumatra benzointree Nutrition 0.000 title abstract 3
- 229960002130 benzoin Drugs 0.000 title abstract 3
- 235000019382 gum benzoic Nutrition 0.000 title abstract 3
- GYTMUNSNMBRSEW-UHFFFAOYSA-N hydrogen carbonate;1h-imidazol-1-ium Chemical compound OC(O)=O.C1=CNC=N1 GYTMUNSNMBRSEW-UHFFFAOYSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001291 vacuum drying Methods 0.000 claims abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 3
- 239000012153 distilled water Substances 0.000 claims abstract description 3
- 239000012065 filter cake Substances 0.000 claims abstract description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 18
- -1 phenyl aldehyde Chemical class 0.000 claims description 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- SGZJDICMAIEXMR-UHFFFAOYSA-N 1,3-dibutyl-2h-imidazole Chemical class CCCCN1CN(CCCC)C=C1 SGZJDICMAIEXMR-UHFFFAOYSA-N 0.000 description 1
- RYNROCNODWBDCM-UHFFFAOYSA-N 1,3-diethyl-2h-imidazole Chemical class CCN1CN(CC)C=C1 RYNROCNODWBDCM-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for catalyzing the preparation of benzoin from benzaldehyde by adopting imidazolium bicarbonate ionic liquid. The method comprises the following steps of: adding the benzaldehyde into tetrahydrofuran, adding an imidazolium bicarbonate ionic liquid catalyst (IL-Cat) which is equivalent to 2%-15% by mole of the benzaldehyde, reacting between room temperature and 80 DEG C for 4h, then performing vacuum distillation, removing a reaction solvent to obtain a white solid, adding distilled water for dispersing the solid, filtering to obtain a filter cake, and performing vacuum drying at 60 DEG C for 8h to obtain the benzoin. The method disclosed by the invention has the advantages of mild conditions, high efficiency, high reaction yield and high selectivity. Compared with the existing method using the ionic liquid, by using the method disclosed by the invention, the addition of any alkaline substances is not required, and the method disclosed by the invention is more economic and environment-friendly.
Description
Technical field
The present invention relates to a kind ofly prepare benzoic method with imidazoles bicarbonate ion liquid catalyst phenyl aldehyde.
Background technology
St-yrax is a kind of important chemical material, be widely used as the anticrater agent of photosensitizers, dyestuff intermediate and the powder coating of photoresist, also be a kind of important medicinal intermediates, as synthetic and diphenylthanedione, diphenylthanedione oxime, the acetic acid st-yrax compounds of antiepileptic drug diphenyl hydantoin.St-yrax can pass through benzoic condensation or bitter almond oil camphor prepared in reaction by phenyl aldehyde.Classical st-yrax is synthetic to be catalyzer (organic reaction with sodium cyanide or potassium cyanide, 1948, (4): 269), though the productive rate height, but toxicity is very big, both destroyed environment, unhealthful again, new improved method uses the coenzyme VITMAIN B1 of biologically active to be catalyzer, this method has simple to operate, conservation, weak point consuming time pollutes characteristics such as light.But reaction needed is operated in ice-water bath, and reaction yield is often lower, and catalyzer is expensive, is not easy to reclaim (university chemistry, 2001,16 (3): 49～50.).Also have report to use Cabbeen to come the catalysis phenyl aldehyde to prepare st-yrax (DE19704273-A1) as catalyzer, but carbone catalyst is expensive and structural instability makes correlation method be difficult to realize industrialization.Begin recent years to occur using ionic liquid to prepare st-yrax as catalyzer, (CN102153525-A, Chem.Lett.2005,16 (3), 321, J.Mol.Catal.A:Chem.2006,256,261, Tetrahedron Lett.2007,48,755 and organic chemistry, 2010,30(6), 912～917), still in all known benzoic reactions of ion liquid catalyzing benzene prepared formaldehyde, all must add a large amount of strong alkaline substances (as potassium tert.-butoxide, sodium hydride, cesium carbonate, potassium hydroxide, salt of wormwood etc.), the adding of these strong alkaline substances has the defective of three aspects: have higher requirement to conversion unit (1); (2) increased raw materials cost; (3) can produce a large amount of wastes after the reaction.
Summary of the invention
The purpose of this invention is to provide a kind of brand-new employing imidazoles bicarbonate ion liquid and prepare benzoic method as the catalyst phenyl aldehyde.With all adopt ionic liquids be the method for catalyzer different be: this method adopts imidazoles bicarbonate ion liquid as catalyzer, uses this catalyst phenyl aldehyde to prepare st-yrax and need not add the productive rate that any alkaline matter can obtain to be satisfied with very much.This method for preparing catalyst is simple, and is cheap and easy to get, and reaction conditions gentleness, benzoic productive rate and selectivity are all very high, almost do not have side reaction and takes place.Can simply reclaim from reaction system by the method for washing after the reaction and obtain imidazoles bicarbonate ion liquid catalyst.
Before the present invention, under the situation that does not add strong alkaline substance, it is impossible fully using ionic liquid to prepare st-yrax as the catalyst phenyl aldehyde.
Technical scheme of the present invention is as follows:
A kind of employing imidazoles bicarbonate ion liquid prepares benzoic method as the catalyst phenyl aldehyde, and its reaction formula is as follows:
It comprises the steps:
Phenyl aldehyde is joined in the tetrahydrofuran (THF) (THF), add the imidazoles bicarbonate ion liquid catalyst (IL-Cat) be equivalent to phenyl aldehyde molar weight 2%～15%, between room temperature～80 ℃, preferred 50 ℃～70 ℃, reaction 4h, then, underpressure distillation is removed reaction solvent and is obtained white solid, add distilled water and make solid dispersed, filter filter cake, 60 ℃ of vacuum-drying 8h can obtain st-yrax.
The employed catalyst I L-Cat of above-mentioned preparation st-yrax method is imidazoles bicarbonate ion liquid, and it has following general formula: [C
mC
n-IM] [HCO
3], its structural formula is as follows:
C wherein
m, C
nBe alkyl substituent, C
m, Cn is a kind of in methyl, ethyl, propyl group, butyl, hexyl or the octyl group, m, n represent the number of substituting group carbon respectively.
A kind ofly prepare above-mentioned imidazoles bicarbonate ion liquid [CmCn-IM] [HCO
3] method is as follows:
The corresponding imidazoles villaumite of imidazoles bicarbonate ion liquid ([CmCn-IM] [Cl]) that will prepare is joined in the suitable methanol solvate, the saleratus or the sodium bicarbonate that add 1.1 times of imidazoles villaumite molar weights, stirring reaction 48h under the room temperature, after reaction finishes, remove by filter sylvite or sodium salt, evaporate to dryness filtrate, 80 ℃ of vacuum-drying 24h obtain imidazoles bicarbonate ion liquid.
The present invention is different from previous invention part and is: this method adopts imidazoles bicarbonate ion liquid catalyst phenyl aldehyde to prepare st-yrax, does not need to add any alkaline matter.The imidazoles supercarbonate preparation method that this method is used is simple, cheap and easy to get, dissolves in conventional organic solvent, have solubleness preferably again in water, and the solubleness in water is often greater than the solubleness in organic solvent.Make that imidazoles bicarbonate ion liquid catalyst can well be dissolved in reaction system in the reaction process, just can from reaction system, remove catalyzer and finish the back in reaction by the method for simple washing, and then steam except moisture the i.e. recyclable catalyzer that obtains.
Embodiment
Following embodiment will describe more comprehensively to the present invention.
Embodiment 1
Add THF100mL in the eggplant-shape bottle of 150ml, (0.2mol 21.224g), adds 1,3-dibutyl imidazoles supercarbonate ([C to phenyl aldehyde
4C
4-IM] [HCO
3]) (0.02mol, 4.846g), under 80 ℃ of water-baths, reaction 4h.Reaction finishes the back solvent evaporated, adds 50g water and stirs 10 minutes, filters out solid, and vacuum drying gets solid 19.158g, fusing point: 135.5～137.8 ℃, and productive rate 90.26%
Embodiment 2
Add THF100mL in the eggplant-shape bottle of 150ml, (0.2mol 21.224g), adds 1,3-methylimidazole supercarbonate ([C to phenyl aldehyde
4C
4-IM] [HCO
3]) (0.004mol, 0.9692g), under 50 ℃ of water-baths, reaction 4h.Reaction finishes the back solvent evaporated, adds 50g water and stirs 10 minutes, filters out solid, and vacuum drying gets solid 3.767g, fusing point: 136.3～137.9 ℃, and productive rate 17.75%
Embodiment 3
Add THF100mL in the eggplant-shape bottle of 150ml, (0.2mol 21.224g), adds 1,3-diethyl imidazoles supercarbonate ([C to phenyl aldehyde
4C
4-IM] [HCO
3]) (0.03mol, 7.269g), in room temperature, reaction 4h.Reaction finishes the back solvent evaporated, adds 50g water and stirs 10 minutes, filters out solid, and vacuum drying gets solid 13.728g, fusing point: 136.3～137.6 ℃, and productive rate 64.68%
Embodiment 4～14
Method similar embodiment 1 adopts different imidazoles bicarbonate ion liquid as catalyzer, the results are shown in Table 1:
Table 1
| Embodiment | IL-cat | Productive rate % |
| 4 | [C 3C 3-IM][HCO 3] | 86.68 |
| 5 | [C 2C 2-IM][HCO 3] | 82.67 |
| 6 | [C 6C 6-IM][HCO 3] | 14.25 |
| 7 | [C 1C 2-IM][HCO 3] | 42.82 |
| 8 | [C 1C 3-IM][HCO 3] | 85.92 |
| 9 | [C 1C 4-IM][HCO 3] | 83.81 |
| 10 | [C 1C 6-IM][HCO 3] | 88.35 |
| 11 | [C 1C 8-IM][HCO 3] | 84.63 |
| 12 | [C 2C 3-IM][HCO 3] | 90.47 |
| 13 | [C 2C 4-IM][HCO 3] | 75.22 |
| 14 | [C 2C 6-IM][HCO 3] | 36.86 |
The comparative example 15～22
Be outstanding the present invention and existing methods difference, similar embodiment 1 adopts non-imidazoles bicarbonate ion liquid as catalyzer, the results are shown in (table 2), must could obtain the st-yrax product after adding highly basic by the visible conventional ion liquid of table.
Table 2
| Embodiment | 10mol%IL-cat | Productive rate % |
| 15 | [C 4C 4-IM][BF 4] | 0 |
| 16 | [C 4C 4-IM][SCN] | 0 |
| 17 | [C 4C 4-IM][AcO] | 0 |
| 18 | [C 4C 4-IM][NO 3] | 0 |
| 19 | [C 4C 4-IM][Br] | 0 |
| 20 | [C 4C 4-IM][NO3]+K 2CO 3* | 34.71 |
| 21 | [C 4C 4-IM][Br]+DBU* | 66.97 |
| 22 | [C 4C 4-IM]Br]+K 2CO 3* | 89.57 |
Remarks: * represents among this embodiment, adds organic bases or mineral alkali when adding catalyzer simultaneously, and the amount that adds alkali is 20% of phenyl aldehyde molar weight, and the remaining reaction condition is identical with embodiment 1 with process.
Claims (3)
1. one kind is adopted imidazoles bicarbonate ion liquid to prepare benzoic method as the catalyst phenyl aldehyde, it is characterized in that it comprises the steps:
Phenyl aldehyde is joined in the tetrahydrofuran (THF), add the imidazoles bicarbonate ion liquid catalyst (IL-Cat) that is equivalent to phenyl aldehyde molar weight 2%～15%, between room temperature～80 ℃, reaction 4h, then, underpressure distillation, remove reaction solvent and obtain white solid, add distilled water and make solid dispersed, filter filter cake, 60 ℃ of vacuum-drying 8h can obtain st-yrax.
2. according to the benzoic method of the described preparation of claim 1, it is characterized in that: employed catalyst I L-Cat is imidazoles bicarbonate ion liquid, and it has following general formula: [C
mC
n-IM] [HCO
3], its structural formula is as follows:
C wherein
m, C
nBe alkyl substituent, C
m, Cn is a kind of in methyl, ethyl, propyl group, butyl, hexyl or the octyl group, m, n represent the number of substituting group carbon respectively.
3. according to the benzoic method of the described preparation of claim 1, it is characterized in that: temperature of reaction is 50 ℃～70 ℃.
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| CN2013101685266A CN103242153A (en) | 2013-05-08 | 2013-05-08 | Method for catalyzing preparation of benzoin from benzaldehyde by adopting imidazolium bicarbonate ionic liquid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109665953A (en) * | 2018-12-21 | 2019-04-23 | 盐城锦明药业有限公司 | A method of preparing styrax class compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5780338A (en) * | 1980-11-07 | 1982-05-19 | Sumitomo Chem Co Ltd | Preparation of benzoin |
| CN101219939A (en) * | 2008-01-17 | 2008-07-16 | 上海华谊丙烯酸有限公司 | Method for synthesizing hydroxyl radical pivalic aldehyde with alkalescence ion liquid catalysis |
| CN102702023A (en) * | 2012-05-14 | 2012-10-03 | 清华大学 | Synthesis method of trans-alpha-benzoinoxime |
-
2013
- 2013-05-08 CN CN2013101685266A patent/CN103242153A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5780338A (en) * | 1980-11-07 | 1982-05-19 | Sumitomo Chem Co Ltd | Preparation of benzoin |
| CN101219939A (en) * | 2008-01-17 | 2008-07-16 | 上海华谊丙烯酸有限公司 | Method for synthesizing hydroxyl radical pivalic aldehyde with alkalescence ion liquid catalysis |
| CN102702023A (en) * | 2012-05-14 | 2012-10-03 | 清华大学 | Synthesis method of trans-alpha-benzoinoxime |
Non-Patent Citations (2)
| Title |
|---|
| MURAT EMRAH MAVIS等: "An investigation of the catalytic potential of mono- and dicationic imidazolium N-heterocyclic carbenes in the benzoin condensation", 《TETRAHEDRON LETTERS》 * |
| 赵三虎等: "咪唑类离子液体催化的安息香缩合反应", 《有机化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109665953A (en) * | 2018-12-21 | 2019-04-23 | 盐城锦明药业有限公司 | A method of preparing styrax class compound |
| CN109665953B (en) * | 2018-12-21 | 2022-09-13 | 盐城师范学院 | Method for preparing benzoin compounds |
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Application publication date: 20130814 |