Study on Synthesis of Hexaarylbisimidazole as Phototropic Material
0
Citation
0
Reference
20
Related Paper
Abstract:
Bis(p-methoxyphenyl)-4,4′-5,5′-tetraphenyl-1,2′-biimidazole (2) was prepared from benzil, p-methoxybenzaldehyde and ammonium acetate. Experiments were done under different reaction conditions, and the optimal conditions were determined. In acetic acid, as mole ratio of benzil, p-methoxybenzaldehyde and ammonium acetate was 1∶1∶8, 93.6% of 2-(p-methoxyphenyl)-4,5-diphenylimidazole (1) was obtained after refluxing for 3 h. When reaction temperature was 0～15 °C, 1 was dissolved in HOCH_2CH_2OCH_2CH_3 and mole ratio of 1 to K_3[Fe(CN)_6] was 1∶2, the yield of 2 was 87.5% after reacting for 5 h.Keywords:
Benzil
Mole
Cite
Studies on Synthesis of 2,2-Bis(3-Phenyl-4-Hydroxypheny) Propane Catalyzed by p-Toluenesulfonic Acid
The 2,2-bis(3-phenyl-4hydroxypheny)propane(bis OPP-A) was synthesized from o-phenyl phenol(OPP) and acetone by using p-Toluenesulfonic acid as main catalyst and 3-mercaptopropanesulfonic acid as promoter.The effects of the reaction temperature and reaction time,the dosages of p-toluene sulfuric acid and 3-mercaptopropanesulfonic acid,the molar ratio of OPP to acetone on the yield of bis OPP-A were studied.The optimum conditions were found as follows: n(acetone):n(o-phenyl phenol):n(p-Toluenesulfonic cid):n(3-mercaptopropanesulfonic acid)=1:4:0.25:0.25,reaction time is 7h and reaction temperature is 60℃,and the yield of 2,2-bis(3-phenyl-4hydroxypheny)propane is 74.2%,the purity of the product is 99.5%.The structure of obtained bisOPP-A was characterized by melting point,IR and 1H-NMR.
p-Toluenesulfonic acid
Propane
Molar ratio
Cite
Citations (0)
o-Nitrophenylacetic acid was synthesized by condensation of o-nitrotoluene with diethyl oxalate catalyzed by C_2H_5ONa,followed by hydrolysis,oxidation with H_2O_2 and acidification with HCl,resulting in an approximate 62% yield.Indazole was synthesized in 71% yield by keeping the diazonation solution for 24 h at room temperature,which was prepared from reducing o-nitrophenylacetic acid with 8%(NH_4)_2S solution upon refluxing for(2 h) and diazotizing with HCl and NaNO_2.The overall yield was around 44%.
Indazole
Cite
Citations (0)
C-Methyl 4,10,16,22-tetramethoxycalix[4]arene has been synthesized from phenol. The reaction performed consisted of methylation of phenol, acetylation of methyl phenyl ether, reduction of p-methoxyacetophenone, and cyclization of p-methoxy-(1-hydroxyethyl)benzene to form C-methyl-4,10,16,22-tetramethoxycalix[4]-arene using BF3-methanol as the acid catalyst. Methylation of phenol was done by reacting phenol with solution of NaOH to generate sodium phenoxide salt. This mixture was strirred at reflux for 0.5 hours. Dimethyl sulphate was added and the reflux was continued for 2,5 hours. The product obtained was methyl phenyl ether, which was found as a colorless liquid in 99.0% yield. Acetylation of methyl phenyl ether was carried out in chloroform using acetic anhydride as the acetylating agent and anhydrous aluminium chloride as the catalyst. The addition of acetic anhydride and anhydrous aluminium chloride was done in two portions. The first portion was 0.967 g of acetic anhydride and 1.4 g of anhydrous aluminium chloride. The second portion was 0.54 g of acetic anhydride and 0.6 g of anhydrous aluminium chloride. The product obtained was found as a reddish yellow liquid in 69.6% yield. Reduction of p-methoxyacetophenone as the acetylation product was done using NaBH4 in ethanol at reflux for 2.5 hours. From this reaction, p-methoxy-(1-hydroxyethyl)benzene was obtained as a brown viscous liquid in 44.9% yield. Cyclization of p-methoxy(1-hydroxyethyl)benzene was done using BF3-methanol as the acid catalyst for two days at room temperature. The product obtained from this cyclization was found as a brown very viscous liquid in 87.3% yield. Identification of reaction products were carried out using Infra Red (IR) Spectrophotometer, Proton Nuclear Magnetic Resonance (1H NMR) spectrometer and Gas Chromatography-Mass spectroscopy (GC-MS). Keywords: synthesis, calix[4]arene, cyclization, and catalyst.
Anhydrous
Aluminium chloride
Acetyl chloride
Sodium bisulfite
Cite
Citations (0)
First,2-methylbutyryl chloride was prepared from 2-methylbutyric acid and thionyl chloride.Second,2-methyl-1-phenyl-1-butanone was synthesized from benzene and 2-methylbutyryl chloride in the presence of anhydrous aluminum chloride as catalyst.Thirdly,2-methyl-2-hydroxy-1-phenyl-1-butanone was prepared by chlorination and hydrolysis of 2-methyl-1-phenyl-1-butanone in the presence of NaOH(aq) with CCl_4 as chlorinating agent and tetrabutyl ammonium bromide as phase transfer catalyst.The experimental results showed that the optimum conditions were as follows: anhydrous aluminum chloride was 22 g,reaction time was 1.5 h,dropwise time of 2-methylbutyryl chloride was 1.5 h,n(C_6H_6)/n(2-methylbutyryl chloride) was 5.0∶1.The yield of 2-methyl-1-phenyl-1-butanone was 92.6%.When CCl_4 was 12 mL,tetrabutyl ammonium bromide was 6 g,sodium hydroxide was 17%,and reaction time was 6 h,the yield of 2-methyl-2-hydroxy-1-phenyl-1-pentanone was 90.3%.The structure of the product was characterized by elemental analysis,IR and MS.
Anhydrous
Ammonium chloride
Butanone
Thionyl chloride
Ammonium bromide
Ammonium hydroxide
Cite
Citations (0)
Phototropic material 2,2′ bis(o chlorophenyl) 4,4′ 5,5′ tetraphenyl 1,2′ biimidazole(HABI) was prepared from benzil and o chlorobenzaldehyde through cyclization and oxidation reactions.Experiments were done under different conditions of the oxidation reaction and the optimal conditions were determined.At 20-25 ℃,the cyclization product 2 (o chlorophenyl) 4,5 diphenylimidazole(TAI) was solvated in HOCH 2CH 2OCH 2CH 3 and oxidized at mole ratio of TAI to K 3)=1∶2 to give HABI in 84 9% yield after reacting for 5 h.
Benzil
Cite
Citations (1)
1,2,4-Triazole potassium salt was prepared from 1,2,4-triazole and potassium hydrate using toluene as the water-carrying agent.Then using acetonitrile as the solvent,2-(1H-1,2,4-triazol-l-yl) acetamide was synthesized from 1,2,4-triazole potassium salt and 2-chloro-N-methylacetamide,which was prepared from methyl 2-chloroacetate and methylamine.The effects of reaction temperature,reaction time and molar ratio of materials on preparation of 2-(1H-1,2,4-triazol-1-yl) acetamide from 1,2,4-triazole potassium salt and 2-chloro-N-methylacetamide were investigated.The optimal reaction conditions were obtained as follows: reaction temperature around 80 ℃,reaction time 4 h,n(1,2,4-triazole potassium salt)∶n(2-chloro-N-methylamine)=1.3∶1.The yield of 2-(1H-1,2,4-triazol-l-yl) acetamide was(87.5%.) The product was characterized by ~1H NMR,MS,IR and elemental analysis.
Acetamide
Proton NMR
Cite
Citations (0)
3-(bis(2-hydroxybenzyl)amino)propanenitrile was synthesized in this paper by the reaction of salicylaldehyde,ammonium hydroxide and acrylonitrile in three steps,in which 2-[(E)-((2-hydroxybenzyl)imino)methyl]phenol was synthesized by the reaction of salicylaldehyde and ammonium hydroxide in 6 hours with the molar ratio of 1∶4 with the yield of 98.2%. 2,2′-(iminobis(methylene))diphenol was synthesized by the reaction of 2-[(E)-((2-hydroxybenzyl)imino)methyl]phenol and KBH4 in 12 hours at 30 ℃ with the molar ratio of 1∶4,and the yield is 84.2%.3-(bis(2-hydroxybenzyl)amino)propanenitrile was synthesized by the reaction of 2,2′-(iminobis(methylene))diphenol and acrylonitrile in 72 hours under reflux with the molar ratio of 1∶6,and the yield is 88%.The products were characterized by the infrared method and X-ray diffraction single crystal structure analysis.
Salicylaldehyde
Ammonium hydroxide
Methylene
Molar ratio
Cite
Citations (0)
The 2,2-bis(3-phenyl-4-hydroxyphenyl) propane(bisOPP-A) was synthesized from o-phenylphenol and acetone by using hydrochloric acid as catalyst and 3-mercaptopropanesulfonic acid as catalytic promoter. The effect of molar ratio of starting materials,the reaction temperature and time on the reaction were studied. The optimum conditions for the synthesis of bisOPP-A are as follows:n(o-phenylphenol):n(acetone):n (hydrochloric acid):n(3-mercaptopropanesulfonic acid) =8:2:4:1,reaction temperature is 60℃and reaction time is 24h,and the yield of bisOPP-A is 78.5%,the purity of the product after recrystaUization is 99.2%.The product was assigned by IR and ~1HNMR.
Hydrochloric acid
Propane
Molar ratio
Cite
Citations (0)
(z)-2-(2-Aminothiazol-4-yl)-2-(2-tert.butoxycarbonylrop-2-oxyimino)acetic acid is obtained from compound(I) by selective hydrolyzation under the alkaline condition. The effects of synthesis conditions such as the ratio of the solvent, the amount of sodium hydroxide, the reaction of temperature on the yield were researched. The optimum conditions were: solvent ratio V(methanol )/V (water) = 2∶1,about 500 mL; and n [compound(I)]: n(sodium hydroxide)= 1∶1.6,reaction temperature,45～50 ℃; reaction time 8 h. The yield of the product is up to 86%。
Sodium hydroxide
Cite
Citations (0)
5-(1-methylthio)ethyl-2-(trifluoromethyl)pyridine(3)was synthesized from 1-(3-methylthiobut-1-phenyl)pyrrolidine(1)and 4-ethoxy-1,1,1-trifluoro-but-3-en-2-one(2)in the protection of nitrogen and presence of ammonium formate. The yield of the reaction was about 63.5% with the purity of 98.6%. The effect of the reaction conditions on reaction yield was investigated,and the optimal conditions were as follows:the material ratio of n(1-(3-methylthiobut-1-phenyl)pyrrolidine)∶n(4-ethoxy-1,1,1-trifluoro-but-3-en-2-one)∶ n(ammonium bicarbonate)=0.9∶1.0∶2.2,reaction solvent was acetonitrile,the solvent amount was 250 mL/mol,calefactive reaction temperature was 75 ℃,total reaction time was 4.5 hours.
Pyrrolidine
Cite
Citations (0)