• Title/Summary/Keyword: 치환 페놀

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Synthesis of 2(3H)-Benzofuranone Derivatives from Substituted Phenols Using Methyl 2-chloro-2-(methylthio)acetate (메틸 2-클로로-2-(메틸티오)아세트산을 이용한 치환페놀류로부터 2(3H)-벤조푸란온 유도체의 합성)

  • Choi, Hong-Dae;Kim, Mi-Heun;Shin, Sang-Hoon;Son, Byung-Wha
    • YAKHAK HOEJI
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    • v.40 no.6
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    • pp.640-645
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    • 1996
  • 5-Alkyl-2(3H)-benzofuranones(3a-e) were prepared from Friedel-Crafts reaction of 4-alkylphenols with methyl 2-chloro-2-(methylthio)acetae(1) followed by the treatment of zinc du st-acetic acid. The reaction of disubstituted phenols with 1 in the presence of stannic chloride afforded 3-methyltWa-2(3H)-benzofuranone derivatives(11a-c), which were readily converted into 2(3H)-benzofuranone derivatives(12a-c) by desulfurization with zinc dust-acetic acid.

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Preparation of Liquefied Cellulose and Analysis of Its Components by GC-MS Spectrometry (액화셀룰로오스의 제조 및 GC-MS에 의한 그 성분 분석)

  • 조국란;황병호;공영토;도금현
    • Journal of Korea Foresty Energy
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    • v.19 no.2
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    • pp.86-92
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    • 2000
  • The liquefactions of $\alpha$-cellulose(Sigma Chemical, C-8002, 47H0383) was prepared in the presence of phenol using sulfuric acid as a catalyst under $N_2$ gas protection at $180^{\circ}C$ for 60minutes to examine its components. The ratio of $\alpha$-cellulose to phenol was 1: 6.2(w/w), and that to sulfuric acid was 1: 0.05(g/$m\ell$). The yields of liquefaction were calculated after the liquefied mixtures were passed through 1G4 glass filter. The luquefied product of $\alpha$-cellulose was analyzed using GC-MS Spectormeter. The 12 compounds identified by GC-MS Spectrometer, of which peak area covers 54% as 2,4-dimethyl phenol, p-isopropyl phenol, 1-ethyl-3,5-dimethyl benzene, o-isopropyl phenol, (E)-2,4\` dihydroxy-stilbene, 2,2\`-methylene-bisphenol, 4,4\`-methylenebisphenol, 3-methyl-2-hydroxyphenyl-(E)-2-hydroxyl-4\`-methoxy-stilbene, 1-phyenyl-1-(4\`hydroxyphenyl)methanol phenol derivatives. From this results, the reaction pathways of the liquefaction of cellulose were proposed through electrophilic substitution reaction. Phenol as a solvent might react with the reaction intermediates as well in the cellulose liquefaction.

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Efficient Cyclization of Substituted Diphenols : Application to the Synthesis of Sulforhodamine B (치환 다이페놀의 효율적 고리화 반응: 설퍼로다민B의 합성에의 응용)

  • Park, Min Kyun;Shim, Jae Jin;Ra, Choon Sup
    • Clean Technology
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    • v.21 no.2
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    • pp.102-107
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    • 2015
  • Rhodamine dyes are widely used as fluorescent probes because of their excellent photophysical properties, such as high extinction coefficients, excellent quantum yields, great photostability, relatively long emission wavelengths. A great synthetic effort has been focused on developing efficient and practical procedures to prepare rhodamine derivatives, because for most applications the probe must be covalently linked to another (bio)molecule or surface. Sulforhodamine B is one of the most used rhodamine dyes for this purpose, because it carries two sulfoxy functions which can be easily utilized for binding with other molecules. Recently, we needed an expedient, practical synthesis of sulforhodamine derivatives. We found the existing procedure for obtaining those compounds unsatisfactory, particularly, with the cyclization process of the dihydroxytriarylmethane (1) to produce the corresponding xanthene derivative (2). We report here our findings, which represent modification of the existing literature procedure and provide access to the corresponding xanthene derivative (2) in a high yield. Use of methanol as a co-solvent was found quite effective to prohibit the water molecule produced during the cyclization reaction from retro-cyclizing back to the starting dihydroxytriarylmethane and the yield of the cyclization was increased (up to 84% from less than 20%). The reaction temperature was significantly lowered (80 vs. 135 ℃). Thus, the reaction proceeds in a higher yield and energy-saving manner where the use of reactants and the production of chemical wastes is minimized.

Synthesis of new N2O2 tetradentate ligands and the substituent effect on the stability constants of the transition metal complexes (새로운 산소-질소(N2O2)계 네 자리 리간드의 합성과 전이금속 착물 안정도상수에 대한 치환기 효과)

  • Kim, Sun Deuk;Jin, Gyoung Rok
    • Analytical Science and Technology
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    • v.19 no.2
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    • pp.131-141
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    • 2006
  • Hydrobromic acid salt of a $N_2O_2$ tetradentate ligand, N,N'-bis(2-hydroxybenzyl)-ethylene-diamine ($H-BHE{\cdot}2HBr$) was synthesized. $Br-BHE{\cdot}2HBr$, $Cl-BHE{\cdot}2HBr$, $CH_3-BHE{\cdot}2HBr$ and $CH_3O-BHE{\cdot}2HBr$ having Br, Cl, $CH_3$ and $CH_3O$ substituents at 5-position of the phenol group of $H-BHE{\cdot}2HBr$ were also synthesized. $Nap-BHE{\cdot}2HBr$ having naphthalen-2-ol instead of the phenol group was also synthesized. The potentiometry study in aqueous solution revealed that the proton dissociations of the synthesized ligands occurred in four steps and the order of the calculated overall proton dissociation constants (${\log}{\beta}_p$) of each ligand was Br-BHE < Cl-BHE < H-BHE < Nap-BHE < $CH_3$-BHE < $CH_3O$-BHE. The order showed a similar trend to that of Hammett substituent constants(${\sigma}_P$). The order of the stability constants (${\log}K_{ML}$) was CO(II) < Ni(II) < Cu(II) > Zn(II) > Cd(II) > Pb(II). The order in their stability constants (${\log}K_{ML}$) of each transition metal complex agreed well with that of the overall proton dissociation constants (${\log}{\beta}_p$).

Kinetics and Mechanism of Nucleophilic Addition of Sodium Thiophenoxide to $\alpha$-(n-Butyl)-N-Phenylnitrone Derivatives ($\alpha$-(n-Butyl)-N-Phenylnitrone 유도체에 대한 Sodium Thiophenoxide의 친핵성 첨가반응 메카니즘과 그의 반응 속도론적 연구)

  • Lee, Gwang Il;Lee, Seok U;Gwak, Cheon Geun;Kim, Yeong Ju;No, Seung Il;Lee, Gi Chang
    • Journal of the Korean Chemical Society
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    • v.38 no.6
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    • pp.442-448
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    • 1994
  • The rate constants of the nucleophilic reaction of ${\alpha}$-(n-butyl)-N-phenylnitrone and its derivatives have been determined by ultraviolet spectrophotometry at $25^{\circ}C$ and a rate equation which can be applied over a wide pH range was obtained. Final product of the addition reaction was $\alpha$-phenylthiobutylidene-aniline. Base on the rate equation, genernal base effect, substituent effect and final product, plausible mechanism of addition reaction have been proposed. Below pH 3.0 the reaction was inititated by the addition of thiophenol, and in the range of pH 3.0∼10.0, proceeded by the competitive addition of thiophenol and thiophenoxide anion. Above the pH 10.0, the reaction proceeded through the addition of a thiophenoxide anion.

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The Effect of Electron Donor on Reductive Dechlorination of Chlorophenols (염소계페놀의 환원적 탈염소화에서의 전자공여체의 영향)

  • 박대원;김성주박정극
    • KSBB Journal
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    • v.11 no.2
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    • pp.211-217
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    • 1996
  • Batch experiments were conducted to investigate the effect of electron donor on reductive dechlorination of 2,4,5-trichlorophenol by a methanogenic consortium. The methanogenic consortium was obtained from the anaerobic digester of a municipal wastewater treatment plant. The batch reactor containing methanogenic consortium was spiked with 2,4,6-trichlorophenol at 10 mg/$\ell$. Acetate, ethanol, glucose of methanol, each was added as an electron donor for methanogenic consortium. During the course of the experiments liquid samples were taken from the batch reactor to measure dechlorination rate and find the dechlorination pathway of 2,4,6-trichlorophenol. After incubation 2,4,6-trichlorophenol was first dechlorinated to 2,4-dichlorophenol and then to 4-chlorophenol. Phenol was not detected in the batch reactor the highest rate of dechlorination of 2,4,6-trichlorophenol was observed when ethanol was used as an electron donor.

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Determination of Reactivity by MO Theory (XXII). MO Studies of Substituent Effects of Rates of Phenylthiyl Radical Additions to ${\alpha}$-Methylstyrene (分子軌道論에 의한 反應性 決定 (제22보). ${\alpha}$-Methylstyrene 에 대한 Phenylthiyl Radical 부가반응에서의 치환기 효과에 관한 分子軌道論的 연구)

  • Ikchoon Lee;Young Gu Cheun
    • Journal of the Korean Chemical Society
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    • v.26 no.1
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    • pp.1-6
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    • 1982
  • The addition of thiophenol to ${\alpha}$-methylstyrene has been studied MO theoretically using CNDO/2 method. Although overall reaction proceeds in two steps i.e., (1) decomposition of thiophenol to give phenylthiyl radical and (2) addition of the radical to ${\alpha}$-methylstyrene to give a new monomer radical, theoretical results suggested that the phenylthiyl radical formation step, (1), was the dominant process in determining the rate of addition; this was the rationale behind the negative ${\rho}$ value obtained experimentally from the Hammett plots for substituents on the thiyl radicals. The departure from a linear Hammett plot for addition of ${\rho}$-chlorophenylthiyl and m-trifluoromethyl phenylthiyl to ${\rho}$-methoxy-${\alpha}$-methylstyrene could be explained as a result of an increased contribution of the addition step, (2) to the overall reaction rate.

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The Photoreactivity of 2-Halobenzyl Phenyl Ether (2-할로벤질 페닐 에델의 광반응성)

  • Park, Yong Tae;Kim, Young Hee;Shin, Hyun Il
    • Journal of the Korean Chemical Society
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    • v.42 no.2
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    • pp.203-208
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    • 1998
  • The photochemical reactivities of 2-halobenzyl phenyl ether, in which 2-halobenzyl moiety are tethered to phenyl moiety by the etheral alkyl linkage, has been studied. In the presence of nitrogen, the photochemical reaction of 2-chlorobenzyl phenyl ether (1) produces mainly phenol and photo-Fries type reaction products, while the corresponding bromo analog 2 produces photocyclization and photoreduced products, along with phenol and photo-Fries type products. The former result implies that since chlorine is bound to the benzyl ring firmly, the rather weaker $CH_{2}-O$ bond of 1 is cleavaged to produce the photo-Fries type product. The latter implies that the photoinduced fission of phenyl-bromine bond of 2 can compete with the fission of $CH_{2}-O$ bond, since the bond energy of phenyl-bromine is lower than that of phenyl-chlorine. Since by the presence of oxygen the formation of phenol is not affected much, the formation of photo-Fries type products is changed a little, and the formations of photocyclization and photoreduced products are affected effectively, a singlet state is involved in the formation of phenol, and both singlet and triplet state may be involved in the formation of photo-Fries type reaction, while a triplet state is involved in the formation of photocyclization and photoreduction products.

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Effect of Korean Red Ginseng on the Stability of the Tight Junction of Intestinal Epithelial Cells (홍삼에 의한 Caco-2 단세포층 간극의 안정화)

  • Shon, Dong-Hwa;Kim, Mi-Hye;Kim, Young-Chan;Kim, Sung-Soo
    • Korean Journal of Food Science and Technology
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    • v.42 no.3
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    • pp.335-342
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    • 2010
  • Bioactive components involved in the tight junction stabilization of intestinal epithelial cells from Korean red ginseng were studied by analyzing transepithelial electrical resistance (TEER) values of the Caco-2 cell monolayer between the apical and basolateral sides for 96 hr. The treatment with less than $20\;{\mu}g/mL$ of the Korean red ginseng extract to the apical side of Caco-2 cell monolayer gave higher TEER values than the control. However, the treatment with more than $130\;{\mu}g/mL$ of the Korean red ginseng extract drastically decreased the TEER values, and these effects were not due to its cytotoxicity. When fractions of low molecular weight compounds, polysaccharides, proteins, saponins, and polyphenols derived from Korean ginseng were applied to the apical side of the Caco-2 cell monolayer, polyphenols showed high tight junction stabilizing activity and saponins showed low activity, but the others showed no significant activity. These results suggest that Korean red ginseng might be useful for the prevention of food allergy by stabilizing the tight junction of intestinal epithelial cells leading to hindering absorption of food allergens.

Effect of Storage Conditions on the Quality of Green Tea Beverage (저장 조건이 녹차 음료의 품질에 미치는 영향)

  • Lee, Jung-Min;Lim, Sang-Wook;Cho, Sung-Hwan;Choi, Sung-Gil;Heo, Ho-Jin;Lee, Seung-Cheol
    • Journal of agriculture & life science
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    • v.43 no.3
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    • pp.27-34
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    • 2009
  • Green tea was prepared by soaking 1.5 g of green tea leaves into 100 mL of distilled water at $75^{\circ}C$ for 5 min. The green tea was stored at three different conditions - (A) green tea was stored at not-artificially excluding natural light condition, at natural air condition, and without addition of vitamin C; (B) green tea was stored at artificially excluding natural light condition by wrapping a vial with aluminium foil, at nitrogen filling up condition, and with addition of 30 mg/100 mL of vitamin C; and (C) green tea was stored at artificially excluding natural light condition by wrapping a vial with aluminium foil, at nitrogen filling up condition, and without addition of vitamin C. After 28 days of storage at $4^{\circ}C$, the chemical quality of the green tea was evaluated. Total phenolic contents of (A), (B), and (C) green tea decreased to 71.50, 73.88 and 75.07%, respectively, after storing for 28 days compared to those of beginning state. DPPH radical scavenging activities of (A), (B), and (C) green tea were 87.87, 92.93 and 88.39%, respectively. Epigallocatechin gallate (EGCG), the main active compounds of green tea, contents of (A), (B), and (C) green tea were 130.61, 136.47 and 4.34%, respectively. The results indicated that light, air condition, and vitamin C were significantly important to the chemical quality of green tea during storage.