• Title/Summary/Keyword: Friedel-Crafts

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Synthesis of 2-(2-Fluorenyl)propanoic Acid

  • Choi, Hong-Dae;Geum, Dek-Hyun;Kowak, Young-Sil;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • v.17 no.1
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    • pp.17-20
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    • 1994
  • Friedel-Crafts reaction of fluorene with methyl ${\alpha}$-chloro-${\alpha}$-(methylthio)acetate 1 gave methyl $\alpha$-methylthio-2-fluoreneacetate 2. Cicloprofen 8, a potent antiinflammatory agent, was prepared by methylation of 2 followed by reductive desulfurization of methyl 2(2-fluorenyl)-2-(methylthio)propionate 6 and hydrolysis of methyl 2-(2-fluorenyl)propionate 7.

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Total Synthesis of Norneolignans from Krameria Species

  • Seo , Pil-Ja;Choi, Hong-Dae;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1189-1193
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    • 2004
  • The total synthesis of norneolignans isolated from Krameria species, 2-aryl-5-(E)-propenylbenzofurans (5, 11), is described. The key step involves the one-pot reaction for 2-arylbenzofurans (2, 7) from 4-hydroxyphenylacetone with 4'-acetoxy-2-chloro-2-(methylthio)acetophenone (1) and 2-chloro-2-methylthio-(2',4',6'-trimethoxy)acetophenone (6) under Friedel-Crafts reactionconditions.

Polystyrene Supported Al(OTf)3: an Environmentally Friendly Heterogeneous Catalyst for Friedel-Crafts Acylation of Aromatic Compounds

  • Boroujeni, Kaveh Parvanak
    • Bulletin of the Korean Chemical Society
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    • v.31 no.11
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    • pp.3156-3158
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    • 2010
  • Stable and non-hygroscopic polystyrene supported aluminium triflate (Ps-$Al(OTf)_3$), which is prepared easily from cheap and commercially available compounds was found to be an environmentally friendly heterogeneous catalyst for Friedel-Crafts acylation of arenes using acid chlorides in the absence of solvent under mild reaction conditions. The catalyst can be reused up to five times after simple washing with dichloromethane.

Synthesis of Novel Mercaptophenyl Carbocyclic C-Nucleoside Analogue Using Sequential [3,3]-Sigmatropic Rearrangement and Ring-closing Metathesis

  • Li, Hua;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.29 no.4
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    • pp.847-850
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    • 2008
  • Novel mercaptophenyl carbocyclic C-nucleoside analogue was synthesized via a cyclopentenol intermediate 10, which was prepared using a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM). Friedel-Crafts alkylation was then used to couple the thiophenol.

Regioselective Friedel-Crafts Reaction of Allyldichlorosilane with 3,4-Benzo-1,1-dichloro-1-dichloro-1-silacyclopentene

  • 박영태;박상욱;김호창
    • Bulletin of the Korean Chemical Society
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    • v.16 no.12
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    • pp.1208-1212
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    • 1995
  • A 86:14 isomeric mixture of 3,4-[3'-(dichlorosilyl)isopropyl]benzo-1,1-dichloro-1-silacyclopentene and 3,4-[2'-(dichlorosilyl)isopropyl]benzo-1,1-dichloro-1-silacyclopentene was prepared by the regioselective Friedel-Crafts reaction of allyldichlorosilane with 3,4-benzo-1,1-dichloro-1-silacyclopentene catalyzed by Lewis acid AlCl3. The structure of the products was confirmed by methylation with methylmagnesium bromide and by methoxylation with trimethylorthoformate.

Synthesis of p-(Acetylamino)phenylacetic acid As an Antirheumatic Agent (항류우머티즘 물질인 p-(아세틸아미노)페닐아세트산의 합성)

  • Choi, Hong-Dae;Son, Byung-Wha
    • YAKHAK HOEJI
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    • v.41 no.4
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    • pp.480-483
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    • 1997
  • The efficient synthesis of p-(acetylamino)phenylacetic acid(7), a antirheumatic agent, is reported. Methyl phenylacetate(3) was prepared from Friedel- Crafts reaction of benzene with methyl ${\alpha}$-chloro-${\alpha}$-(methylthio)acetate(1) followed by reductive desulfurization with zinc dust in acetic acid. Compound(7) was obtained from 3 by a sequence of nitration, reduction, N-acylation, and hydrolysis.

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The Risk Assessment of Runway Reaction in the Process of Fridel-Crafts Acylation for Synthesis Reaction (화합물 합성반응 중 Fridel - Crafts Acylation 공정에서의 폭주반응 위험성평가)

  • Lee, Kwangho;Kim, Wonsung;Jun, Jinwoo;Joo, Youngjong;Park, Kyoshik
    • Journal of the Korean Society of Safety
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    • v.36 no.3
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    • pp.24-30
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    • 2021
  • Heat is generated during the synthesis and mixing process of chemical compounds due to a change in activation energy during the reaction. A runaway reaction occurs when sufficient heat is not removed during the heat control process within a reactor, rapidly increasing the temperature, reaction speed, and rate of heat generation inside the reactor. A risk assessment was executed using an RC-1 (Reaction Calorimeter) during Friedel-Crafts acylation. Friedel-Crafts acylation runs the risk of rapid heat generation during Active Pharmaceutical Ingredient (API) manufacturing; it was used to confirm the risk of a runaway reaction at each synthesis stage and during the mixing process. This study used experimental data to develop a safety efficiency improvement plan to control the risks of runaway and other exothermic reactions, which was implemented at the production site of a chemical plant.