• Title/Summary/Keyword: Friedel-Crafts

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Synthesis of 4-(2-thiazolyloxy)phenylalkanoic Acids As An An-tiinflammatory Agent

  • Choi, Hong-Dae;Shin, Sang-Hoon;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • v.19 no.2
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    • pp.148-152
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    • 1996
  • The efficient synthesis of 4-(2-thiazolyloxy)phenylalkanoic acids (10a-c), which are a potent antiinflammatory agent, was achieved in 5-6 steps starting from isopropoxybenzene and methyl $\alpha-chloro-\alpha-(methylthio)acetate (1)$. The key intermediate (4) was prepared by Friedel-Crafts reaction of isopropoxybenzene with (1) followed by desulfurization and the removal of isopropyl protector. Methyl 4-hydroxyphenylalkanoates (6, 8) were similarly obtained from alkylation of (3) and deprotection.

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Synthesis of Hexaprofen [2-(4-Cyclohexylphenyl) propionic Acid]

  • Choi, Hong-Dae;Ma, Jung-Joo;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • v.15 no.2
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    • pp.142-145
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    • 1992
  • A novel preparative method for hexaprofen, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of cyclohexylbenzene with ethyl $\alpha$-chloro-$\alpha$-(methylthio) acetate 1 and $\alpha$-chloro-$\alpha$-(methylthio) acetonitrile 2 afforded ethyl 2-(methylthio)-2-(4-cyclohexylphenyl) acetate 7 and 2-methylthio-2-(4-cyclohexylphenyl) acetonitrile 8, respectively. Compounds 7 and 8 were converted into the corresponding ethyl 2-methylthio-2-(4-cyclohexylphenyl) propionate 9 and 2-methylthio-2-(4-cyclohexylphenyl) propionitrile 10 by methylation with sodium hydride and methyl iodide. Hexaprofen 13 was prepard by hydrolysis of ethyl 2-(4-cyclohexylphenyl) propionate 11 and of 2-(4-cyclohexylphenyl) propionitrile 12 followed by desulfurization of compounds 9 and 10.

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Preparation and Characterization of Poly(phenylene sulfide)-Functionalized MWNTs (폴리(페닐렌 설파이드)로 기능화된 다중벽 탄소나노튜브의 제조와 특성분석)

  • Hong, Sung Yeon;Kim, Young Ho
    • Polymer(Korea)
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    • v.38 no.6
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    • pp.791-800
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    • 2014
  • 4-Chlorobenzoyl (CB) group-attached multi-walled carbon nanotube (c-MWNT) was prepared via a direct Friedel-Crafts acylation of MWNT with 4-chlorobenzoic acid (CBA) in a $P_2O_5$/poly(phosphoric acid) medium. c-MWNT with a maximum chlorine content of 5.3 wt% (CB group content of 20.9 wt%) was obtained by controlling the amount of CBA during the reaction. Using a self-condensation polymerization of 4-chlorobenzenethiol (CBT) to poly(phenylene sulfide) (PPS), MWNT-g-PPS was prepared by adding c-MWNT of chlorine content of 5.3 wt% during the self-polymerization of CBT and removing homo PPS after polymerization in order to increase the interfacial interaction between PPS and MWNT. Thermal and surface properties of the MWNT-g-PPS were characterized. The results showed that PPS was formed on the surface of c-MWNT by the condensation of c-MWNT and CBT.

Synthesis of Bufexamac (Bufexamac의 합성)

  • Choi, Hong-Dae;Ma, Jung-Jeo
    • YAKHAK HOEJI
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    • v.34 no.3
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    • pp.212-214
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    • 1990
  • A new synthetic method for bufexamac, which is a potent anti-inflammatory agent, was described. Friedel-Crafts reaction of butoxybenzene (2) with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ (1) gave ethyl 2-methylthio-2-(p-butoxyphenyl) acetate (3). Ethyl 2-(p-butoxyphenyl)acetate (4) was prepared by desulfurization of compound (3) with zinc dust-acetic acid. Bufexamac (5) could be easily synthesized by treatment of compound (4) with hydroxylamine HCl.

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Synthesis of Substituted Phenyltrichlorocyclopropene Derivatives Using Friedel-Crafts Reaction

  • Choi, Sam-Kwon;Suk ,Won-Kyung
    • Bulletin of the Korean Chemical Society
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    • v.2 no.3
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    • pp.83-85
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    • 1981
  • Tetrachlorocyclopropene has been prepared smoothly by the dehydrochlorination of pentachlorocyclopropane which could be obtained easily from sodium trichloroacetate and trichloroethylene in 1,2-dimethoxyethane. By the reaction of aromatic hydrocarbons with tetrachlorocyclopropene and aluminium chloride, new substituted phenyltrichlorocyclopropene derivatives have been prepared. The structures of these compounds were characterized by means of spectroscopic methods.