• Title/Summary/Keyword: Friedel-Crafts acylation

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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 4-Phenyltetralone Derivatives and Reaction Mechanism

  • Kwon, Soon-Kyoung;Park, Young-Nam
    • Archives of Pharmacal Research
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    • v.23 no.4
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    • pp.329-331
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    • 2000
  • 4-(p-Chlorophenyl)tetralone (6) and 7-chloro-5-(p-chlorophenyl)tetralone (9) are key intermediates for the development of benzazepinone derivative haftens. These compounds could be synthesized from 4-phenyltetralone derivatives by triflic acid catalyzed Friedel-Crafts reaction. The reaction mechanism of Friedel-Crafts alkylation/acylation with lactones in triflic acid is presented. According to our tentative research, ring opening of protonated lactone (2) occurs in alkyl cleavage and the rate of the reaction is not dependent on concentration of triflic acid. So, alkylation of lactone in Friedel-Crafts reaction is presumed to be $A_{AL}$ 1. In second step, intramolecular acylation of the intermediates 4 to 6, 4 can be transformed to a triflic acid-carboxylic anhydride and then the cyclization is undergone after leaving of the triflate anion.

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Synthesis of 5-(p-Toluoyl)-1-Methylpyrrole-2-Acetic Acid [Tolmetin] (5-(p-톨루오일)-1-메틸피롤-2-아세트산의 합성)

  • Choi, Hong-Dae;Ma, Jung-Joo
    • YAKHAK HOEJI
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    • v.36 no.4
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    • pp.341-344
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    • 1992
  • A facile method for tolmetin, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of 1-methylpyrrole with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ (1) gave ethyl ${\alpha}-methylthio$-1-methyl-2-pyrroleacetate (4), which was readily converted into ethyl 1-methyl-2-pyrroleacetate (5) by reductive desulfurization with zinc dust in acetic acid. Tolmetin was synthesized by Friedel-Crafts acylation of (5) with p-toluoyl chloride, followed by hydrolysis of the resultant ethyl 5-(p-toluoyl)-1-methylpyrrole-2-acetate (6).

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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.

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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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.

Efficient Synthesis of 2-Aminoindan and cis-(${\pm}$)-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one (2-Aminoindan 및 cis- ( ${\pm}$ ) -4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one의 효율적 합성)

  • Kim, Min-Woo;Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.50 no.6
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    • pp.403-408
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    • 2006
  • 1-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3- (3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with hydroxylamine, and reduction with an overall yield of 74%. 2-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3-(3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with isoamylnitrite, reduction in NaOH and reaction with HCI to form 5,6-dimethoxy-2-indanone, which was reacted with hydroxylamine and reduced with an overall yield of 42%. 5,6-Dimethoxyindan-1,2-dione-2-oxime, which was catalytically hydrogenated to afford cis-, and trans-1-amino-5,6-dimethoxyindan-1-ol as 3 : 1 ratio. This mixture was treated with Li and reacted with chloroacetyl chloride. Cis isomer was acylated and cyclized to synthesize rir -( ${\pm}$ )-7,8-dimethoxy-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one, but trans isomer was just acylated to form amide.

Synthesis of 7-[p-(Methylthio)benzoyl]-5-benzofurancetic Acid

  • Choi, Hong-Dae;Geum, Dek-Hyun;Kowan, Youn-Sil;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • v.16 no.4
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    • pp.343-346
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    • 1993
  • A new method was described for the preparation of 7-[p-(methylthio)benzoyl]-5-benzofuranacetic acid 6, which is an analgestic agent. Methyl 5-(2, 3-di-hydobenzofuran)acetate 3 was obtained by Friedel-Crafts reaction of 2, 3-dihydrobenzofuran with methyl .alpha.-chloro-.alpha.(methylthio)actate 1 and desulfurization of 2. Tifurac 6 was synthesized from acylation of 3 with p-(methythio)benzoyl chioride followed by bromination of 4, dehydrohalogenation, and hydrolysis of 5.

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Syntheses of Novel 10-Oxodaunomycinone Derivatives (새로운 10-옥소다우노마이시논 유도체의 합성)

  • 노영쇠;김선자;조인호;신홍식
    • YAKHAK HOEJI
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    • v.43 no.1
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    • pp.11-15
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    • 1999
  • A brief route for regiospecific synthesis of novel 10-Oxodaunomycinone Derivatives (10a, b) is described. Dimethoxy-l-tetralone 4 was converted to acetyl tetralone (5a, b) which was oxidized with oxygen to obtain cis-diol compound (8a, b). The construction of (10a, b) was completed by the condensation of phthaloyl dichloride 9 with cis-diol (8a, b)

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