CN101274877A - 1, 2- diaryl alcohol and preparation - Google Patents
1, 2- diaryl alcohol and preparation Download PDFInfo
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- CN101274877A CN101274877A CNA2008100177966A CN200810017796A CN101274877A CN 101274877 A CN101274877 A CN 101274877A CN A2008100177966 A CNA2008100177966 A CN A2008100177966A CN 200810017796 A CN200810017796 A CN 200810017796A CN 101274877 A CN101274877 A CN 101274877A
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Abstract
The invention provides a new method for synthesis of 1, 2-diaryl alcohol. The method takes activated zinc powder as an accelerator and aromatic aldehyde and benzyl bromide react under room temperature and the protection of nitrogen; quenching reaction is carried out with saturated ammonium chloride solution; then the solution is extracted by using ether and dried; the solvent is steamed out and at last the 1, 2-diaryl alcohol is obtained after column chromatographic separation. The synthesis method of the invention applies cheap nontoxic zinc powder, carries out benzylation of aromatic aldehyde without using catalyst and solvent, reduces pollution of the solvent to the environment and achieves the purpose of green synthesis; the reaction of the method is carried out under room temperature; the reaction condition is moderate and the operation is easy, and therefore the method is conducive to industrial production; the synthetic yield is high and can reach more than 80 percent.
Description
Technical field
The invention belongs to organic chemistry filed, relate to a kind of 1,2-2-diaryl alcohol and preparation method thereof, relating in particular to a kind of utilization is promotor with the metal zinc, utilizes aromatic aldehyde and cylite prepared in reaction 1 at room temperature, the method for 2-2-diaryl alcohol.
Background technology
1, the 2-2-diaryl alcohol is the important organic compound of a class, is crucial synthetic building block in the molecule synthesis of many natural products and biologically active, about its attention of synthesizing the educational circles that extremely organises.
At present, about 1, the report of 2-2-diaryl alcohol synthetic method is a lot.Wherein following several method is used comparatively extensive: first method is a reduction method, itself contains 1 reduction, and the ketone compounds of 2-diaryl structure is as 1,2-phenylbenzene ethyl ketone (Eur.J.Org.Chem., 19,3326-3335), 2-hydroxyl-1,2-phenylbenzene ethyl ketone (Chem.Ber., 7,1651), compound such as diphenylthanedione (Chem.Pharm.Bull., 53,1017-1020).Second method is the open loop method, utilizes the ring-opening reaction of substituted epoxy ethane.As use phenyl ethylene oxide and phenyl-magnesium-bromide in ether, to react generation 1,2-phenylbenzene ethanol (J.Org.Chem., 3,355,359); The reaction of phenyl ethylene oxide and phenyl lithium (J.Am.Chem.Soc., 106,3693-3694); 1,2-phenylbenzene oxyethane and Na (PEG-400)
2BH
2In tetrahydrofuran (THF), reacted 20 hours, the productive rate with 70% obtain 1,2 phenylbenzene ethanol (J.Org.Chem., 52,671-674.).The third method is to utilize the addition of benzyl reagent and aromatic aldehyde.Benzyl reagent comprises benzyl alcohol, benzylic ether, benzyl ester, benzyl-metal thing and the non-metallic thing of benzyl etc., and wherein of paramount importance is Grignard reagent.The addition reaction of benzyl magnesium halide and aromatic aldehyde is the classical way of synthetic this compounds.Addition (Chem.Ber., 45,3189 as phenyl aldehyde and benzyl magnesium halide; J.Chem.Soc.Perkin Trans., 1,323-332.); The addition of phenylacetic aldehyde and phenyl-magnesium-chloride (Org.Lett, 8,773-776).But this method relates to the preparation of Grignard reagent, usually under anhydrous, oxygen free condition, carry out, and will use through ethers (ether, tetrahydrofuran (THF)) organic solvent anhydrous, the strict processing of anaerobic, also need under cold condition, carry out sometimes, bring inconvenience to practical application.
1, the preparation of 2-2-diaryl alcohol also has hydrolysis method, electrolytic process, optical radiation method etc.All these methods have all been used organic solvent, and wherein some method also needs to use conditions such as catalyzer, low temperature; In addition, some method then side reaction is many, and productive rate is low, can not be applied to reality, does not also meet the requirement of Green Chemistry.
Summary of the invention
The purpose of this invention is to provide a kind of is promotor with the metal zinc, utilizes aromatic aldehyde and cylite prepared in reaction 1 at room temperature, the method for 2-2-diaryl alcohol.
(1) 1,2-2-diaryl alcohol
Of the present invention 1,2-2-diaryl alcohol compounds, its chemical structural formula is as follows:
Wherein, R=H, 2-Cl, 2,4-DiCl, 3-Br.
Synthesizing of (two) 1,2-2-diaryl alcohols
The present invention 1; the preparation method of 2-2-diaryl alcohol; be to be promotor with the activatory zinc powder earlier, under protection of nitrogen gas, aromatic aldehyde and cylite reacted under room temperature; carry out the cancellation reaction with saturated aqueous ammonium chloride again; use extracted with diethyl ether at last, drying boils off column chromatography for separation behind the solvent; get 1,2-diaryl ethanol.
Its specific embodiment is as follows:
Aromatic aldehyde and the cylite molar weight with 1: 1.2～1: 1.3 is joined in the exsiccant reactor, under protection of nitrogen gas, add the activated zinc powder of 1.1～1.2 times of molar weights of aromatic aldehyde in reactor, stirring reaction is 1.5～2.5 hours under room temperature; Carry out the cancellation reaction with the saturated aqueous ammonium chloride of 2～3 times of aromatic aldehyde molar weights again, use extracted with diethyl ether then, drying boils off column chromatography for separation behind the solvent, 1,2-diaryl ethanol.
Described aromatic aldehyde is for being phenyl aldehyde, 2-chlorobenzaldehyde, 2,4 dichloro benzene formaldehyde or 3-bromobenzaldehyde.Products obtained therefrom is 1,2-phenylbenzene ethanol, 1-(2-chloro-phenyl-)-2 phenylethyl alcohol, 1-(2,4 dichloro benzene base)-2 phenylethyl alcohol and 1-(3-bromophenyl)-2 phenylethyl alcohol.
Its building-up process is shown below:
Wherein, R=H, 2-Cl, 2,4-DiCl, 3-Br.
The activating process of described zinc powder is: the oxide film of removing the zinc powder surface with dilute hydrochloric acid, water, acetone, anhydrous diethyl ether washing successively, remove inorganic salt and moisture in the zinc powder, 80～100 ℃ of following vacuum-dryings 2～3 hours, promptly get the activatory zinc powder after the cooling then.
The present invention compared with prior art has the following advantages:
1, to adopt the metal zinc of non-toxic inexpensive be promotor in the present invention, utilize aromatic aldehyde and cylite prepared in reaction 1 at room temperature, the method for 2-2-diaryl alcohol is not used any catalyzer and organic solvent, reduced the pollution of solvent and catalyzer, realized environment amenable chemosynthesis environment;
2, reaction of the present invention is at room temperature carried out, and the reaction conditions gentleness is easy to operation, is beneficial to suitability for industrialized production.
3, productive rate height of the present invention: can reach more than 80%; The quality product height: purity is more than 99%.
Embodiment
Embodiment one, 1, the preparation of 2-phenylbenzene alcoholic acid
(1)) activation of zinc powder: remove the oxide film on zinc powder surface with dilute hydrochloric acid, inorganic salt and moisture are removed in water, acetone, anhydrous diethyl ether washing successively, 100 ℃ of following vacuum-dryings 3 hours, promptly get the activatory zinc powder after the cooling.
(2) 1,2-phenylbenzene alcoholic acid preparation: in exsiccant reaction flask (50mL round-bottomed flask), add activatory zinc powder (0.59g, 9mmol), go out the air of the inside with nitrogen replacement after, via dropping funnel add phenyl aldehyde (0.85g, 8mmol), cylite (1.2mL, 10mmol), stirred 2 hours under the room temperature; Reaction finishes the back and add ether in reaction flask, adds saturated aqueous ammonium chloride solution 10mL then, stirs reaction down 10 minutes, makes reaction terminating; Tell organic phase, after water extracted 3 times with ether (10mL), the organic phase of merging was used MgSO
4Drying is carried out column chromatography (silica gel, 300-400 after boiling off solvent; Sherwood oil: ethyl acetate=15: 1), separate pure product 1, the 2-2-diaryl alcohol.Productive rate is: 80%.
The melting range of product: 63～64 ℃.
The ir data of product is as follows:
IR(υ/cm
-1)：3316，3062，3026，2921，2861，1601，1493，1450，1330，1206，1040，949，778，689。
Above-mentioned data show, contain phenyl ring and hydroxyl in the structure of this product.
The nuclear magnetic resonance data of product is as follows:
1H?NMR(400MHz，CDCl
3)：δ＝7.36-7.18(m，10H)，4.89(dd，J＝8.4，4.8Hz，1H)，3.04(dd，J＝13.6，4.8Hz，1H)，2.99(dd，J＝13.6，8.4Hz，1H)，1.86(s，1H)；
13C?NMR(100MHz，CDCl
3)：δ＝143.8，138.0，129.5，128.5，128.4，127.6，126.6，125.9，75.3，46.1。
10 H of proton nmr spectra chemical shift 7.36-7.18 are ten hydrogen on the phenyl ring, and 1 H at 4.89 places is a hydrogen on the tertiary carbon, and 2 H at 3.04 and 2.99 places are two hydrogen on the benzyl, and hydroxyl hydrogen appears at 1.86 places; The 10 class carbon atoms of this product structure all occur in the carbon spectrum.
The mass-spectrometric data of this product is as follows:
EI-MS(m/z，％)：198(M
+，2.9)，122(6.1)，107(73.6)，92(100)，79(63.4)，77(44.5)。
The molecular ion peak that occurs this product in the mass-spectrometric data.
The structural formula of this product is as follows:
The preparation of embodiment two, 1-(2-chloro-phenyl-)-2 phenylethyl alcohol
(1) activation of zinc powder: with embodiment one.
(2) preparation of 1-(2-chloro-phenyl-)-2 phenylethyl alcohol: in exsiccant reaction flask (50mL round-bottomed flask), take by weighing the good zinc powder (0.59g of activation, 9mmol) and the 2-chlorobenzaldehyde (1.12g, 8mmol), under protection of nitrogen gas, in reactor, drip cylite (1.2mL, 10mmol), stirred 2 hours under the room temperature, add 10mL saturated aqueous ammonium chloride cancellation reaction, extracted with diethyl ether (10mL) 3 times, behind anhydrous magnesium sulfate drying, boil off column chromatography (silica gel, 300-400 order behind the solvent; Sherwood oil: ethyl acetate, 15: 1) separates, get pure product 1-(2-chloro-phenyl-)-2 phenylethyl alcohol.Productive rate is: 86%.
The melting range of this product: 69～71 ℃.
The ir data of product of the present invention is as follows:
IR(υ/cm
-1)：3301，3060，3026，2924，2853，1600，1575，1491，1470，1439，1351，1202，1076，1032，748，700，550。
Above-mentioned data declaration contains phenyl ring and hydroxyl in the structure of this product.
The nuclear magnetic resonance data of this product is as follows:
1H?NMR(400MHz，CDCl
3)：δ＝7.58(d，J＝8.0Hz，1H)，7.35-7.19(m，8H)，5.30(dd，J＝9.4，3.2Hz，1H)，3.18(dd，J＝13.6，3.2Hz，1H)，2.75(dd，J＝13.6，9.4Hz，1H)，1.82(s，1H)；
13C?NMR(CDCl
3，100MHz)：δ＝141.2，138.1，131.6，129.5，129.3，128.6，128.5，127.1，127.0，126.7，71.8，44.3。
1 H at proton nmr spectra chemical shift 7.58 places and 8 H at 7.35-7.19 place totally 9 hydrogen are nine hydrogen on the phenyl ring, 5.30 1 H that locates is a hydrogen on the tertiary carbon, 3.18 and 2 H at 2.75 places are two hydrogen on the benzyl, the chemical shift of hydroxyl hydrogen is 1.82; 12 class carbon atoms in the carbon spectrum in this product structure all occur.
The mass-spectrometric data of this product is as follows:
EI-MS(m/z，％)：234(M
++2，0.7)，232(M
+，2.2)，215(0.1)，195(0.1)，165(0.9)，92(100)，77(57.9)。
The molecular ion peak that occurs this product in the mass-spectrometric data.
The results of elemental analyses of this product is as follows:
Anal.Calcd.For?C
14H
13OCl：C，72.26；H，5.63.Found：C，72.49；H，5.87。
The structural formula of this product is as follows:
The preparation of embodiment three, 1-(2,4 dichloro benzene base)-2 phenylethyl alcohol
(1) activation of zinc powder: with embodiment one.
(2) 1-(2, the 4-dichlorophenyl)-and the preparation of 2 phenylethyl alcohol: in exsiccant reaction flask (50mL round-bottomed flask), take by weighing the good zinc powder (0.59g of activation, 9mmol) with 2,4-dichlorobenzaldehyde (1.40g, 8mmol), under protection of nitrogen gas, in reactor, drip cylite (1.2mL, 10mmol), stirred 2 hours under the room temperature, add 10mL saturated aqueous ammonium chloride cancellation reaction, extracted with diethyl ether (10mL) 3 times, behind anhydrous magnesium sulfate drying, boil off column chromatography (silica gel, 300-400 order behind the solvent; Sherwood oil: ethyl acetate=15: 1) separate 1-(2,4 dichloro benzene base)-2 phenylethyl alcohol.Productive rate is: 83%.
The melting range of this product: 105～107 ℃.
The ir data of this product is as follows:
IR(υ/cm
-1)：3301，3060，3026，2924，2853，1600，1575，1491，1470，1439，1351，1202，1076，1032，748，700，550。
Above-mentioned data declaration contains phenyl ring and hydroxyl in the structure of this product.
The nuclear magnetic resonance data of this product is as follows:
1H?NMR(400MHz，CDCl
3)：δ＝7.51(d，J＝8.4Hz，1H)，7.36-7.24(m，7H)，5.23(dd，J＝8.8，3.2Hz，1H)，3.14(dd，J＝14.0，3.2Hz，1H)，2.71(dd，J＝14.0，8.8Hz，1H)，2.00(s，1H)；
13C?NMR(100MHz，CDCl
3)：δ＝139.9，137.6，133.5，132.1，129.5，129.1，128.7，128.1，127.4，126.9，71.4，44.2。
1 H at proton nmr spectra chemical shift 7.51 places and 7 hydrogen at 7.36-7.24 place totally 8 hydrogen are eight hydrogen on the phenyl ring, 5.23 1 H that locates is a hydrogen on the tertiary carbon, 3.14 and 2 H at 2.71 places are two hydrogen on the benzyl, hydroxyl hydrogen appears at 2.00 places; The 12 class carbon atoms of this product structure all occur in the carbon spectrum.
The mass-spectrometric data of product of the present invention is as follows:
EI-MS(m/z，％)：268(M
++2，0.7)，266(M
+，1.3)，175(37.0)，149(6.2)，111(18.2)，91(100)，77(9.2)。
The molecular ion peak that occurs this product in the mass-spectrometric data.
The results of elemental analyses of this product is as follows:
Anal.Calcd.For?C
14H
12OCl
2：C，62.94；H，4.53.Found：C，62.69；H，4.86。
The structural formula of this product is as follows:
The preparation of embodiment four, 1-(3-bromophenyl)-2 phenylethyl alcohol
(1) activation of zinc powder: with embodiment one.
(2) preparation of 1-(3-bromophenyl)-2 phenylethyl alcohol: in exsiccant 50mL flask, add activatory zinc powder (0.59g, 9mmol), go out the air of the inside with nitrogen replacement after, add 3-bromobenzaldehyde (1.48g via dropping funnel, 8mmol), and cylite (1.2mL, 10mmol), stirring is 2 hours under room temperature; Reaction finishes the back and add ether in reaction flask, adds saturated aqueous ammonium chloride solution 10mL then, stirs reaction down 10 minutes, makes reaction terminating; Tell organic phase, water is with after the extracted with diethyl ether 3 times, and the organic phase of merging is used MgSO
4After the drying, boil off column chromatography (silica gel, 300-400 order behind the solvent; Sherwood oil: ethyl acetate=15: 1) separate, get pure product 1-(3-bromophenyl)-2 phenylethyl alcohol.Productive rate is: 81%.
This product is a colourless liquid.
The ir data of product of the present invention is as follows:
IR(υ/cm
-1)：3396，3061，3027，2919，1681，1596，1569，1494，1452，1341，1193，1071，1000，885，783，745，698，626。
Above-mentioned data declaration contains phenyl ring and hydroxyl in the structure of this product.
The nuclear magnetic resonance data of this product is as follows:
1H?NMR(400MHz，CDCl
3)：δ＝7.52(s，1H)，7.41-7.08(m，8H)，4.83(dd，J＝8.6，4.4Hz，1H)，3.01(dd，J＝13.8，4.4Hz，1H)，2.92(dd，J＝13.8，8.6Hz，1H)，1.98(s，1H)；
13C?NMR(100MHz，CDCl
3)：δ＝146.0，137.4，130.6，129.9，129.5，129.0，128.7，126.8，124.5，122.5，74.6，46.1。
1 H at proton nmr spectra chemical shift 7.52 places and 8 H at 7.41-7.08 place totally 9 hydrogen are nine hydrogen on the phenyl ring, and 1 H at 4.89 places is a hydrogen on the tertiary carbon, and 2 H at 3.04 and 2.99 places are two hydrogen on the benzyl, and hydroxyl hydrogen appears at 1.86 places; The 12 class carbon atoms of this product structure in the carbon spectrum all occur.
The mass-spectrometric data of product of the present invention is as follows:
EI-MS(m/z，％)：278(M
++2，0.7)，276(M
+，0.7)，195(0.1)，157(16.0)，92(100)，77(36.0).。
The molecular ion peak that occurs this product in the mass-spectrometric data.
The structural formula of this product is as follows:
Reagent and instrument that product of the present invention is identified: infrared spectrometer is an Alpha Centauri FI-IR type instrument; Nuclear magnetic resonance spectrum is solvent with the Bruker Mercury-Plus 400MHz of company type nmr determination with the deuterochloroform, and TMS is interior mark; Mass spectrum is measured with QP-1000A GC-MS, the EI source; Fusing point test is measured with micro melting point apparatus, and thermometer is not proofreaied and correct; Used aromatic aldehyde is an Alfa Aesar reagent in the experiment, and zinc powder, bromobenzyl and other solvent are homemade A.R. level reagent.
Claims (4)
1,1, the 2-2-diaryl alcohol, its chemical structural formula is as follows:
Wherein, R=H, 2-Cl, 2,4-DiCl, 3-Br.
2, according to claim 11, the preparation method of 2-2-diaryl alcohol is to be promotor with the activatory zinc powder earlier, under protection of nitrogen gas, aromatic aldehyde and cylite is reacted under room temperature; After reaction finishes, carry out the cancellation reaction with saturated aqueous ammonium chloride, use extracted with diethyl ether then, drying boils off column chromatography for separation behind the solvent, 1,2-diaryl ethanol; The mol ratio of described aromatic aldehyde and cylite is 1: 1.2～1: 1.3; The consumption of described activated zinc powder is 1.1～1.2 times of aromatic aldehyde; Reaction times is 1.5～2.5 hours.
3, state 1 as claim 2, the preparation method of 2-2-diaryl alcohol, it is characterized in that: aromatic aldehyde and the cylite molar weight with 1: 1.2～1: 1.3 is joined in the exsiccant reactor, under protection of nitrogen gas, add the activated zinc powder of 1.1～1.2 times of molar weights of aromatic aldehyde in reactor, stirring reaction is 1.5～2.5 hours under room temperature; Carry out the cancellation reaction with the saturated aqueous ammonium chloride of 2～3 times of aromatic aldehyde molar weights again, use extracted with diethyl ether then, drying boils off column chromatography for separation behind the solvent, 1,2-diaryl ethanol.
4, state 1 as claim 2 or 3, the preparation method of 2-2-diaryl alcohol is characterized in that: described aromatic aldehyde is a phenyl aldehyde, or the 2-chlorobenzaldehyde, or 2,4 dichloro benzene formaldehyde, or the 3-bromobenzaldehyde.
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ID=39994782
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114907279A (en) * | 2022-03-29 | 2022-08-16 | 金华职业技术学院 | Synthesis method of N-oxyphenyltriazole |
-
2008
- 2008-03-15 CN CNA2008100177966A patent/CN101274877A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114907279A (en) * | 2022-03-29 | 2022-08-16 | 金华职业技术学院 | Synthesis method of N-oxyphenyltriazole |
| CN114907279B (en) * | 2022-03-29 | 2023-11-10 | 金华职业技术学院 | Synthesis method of N-oxybenzene propyl triazole |
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Open date: 20081001 |