• Bulletin of the Korean Chemical Society
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• 제31권11호
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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.

• Archives of Pharmacal Research
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• 제23권4호
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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.

• 약학회지
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• 제36권4호
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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).

• 한국안전학회지
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• 제36권3호
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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.

• 약학회지
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• 제41권4호
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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.

• Bulletin of the Korean Chemical Society
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• 제28권10호
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• pp.1854-1856
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• 2007

• 폴리머
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• 제38권6호
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• pp.791-800
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• 2014

Friedel-Crafts 직접 아실화 반응을 이용하여 $P_2O_5$/폴리인산 매질에서 다중벽 탄소나노튜브(MWNT)와 4-클로로벤조산(CBA)을 반응시켜 클로로벤조일(CB)기가 도입된 MWNT(c-MWNT)를 제조하였다. 이때 반응시키는 CBA양을 조절하여 염소원자 함량이 최대 5.3 wt%(CB기 함량 20.86 wt%)인 c-MWNT를 얻었다. 한편, 열가소성 엔지니어링 플라스틱 소재인 폴리(페닐렌 설파이드) (PPS)와 MWNT의 계면접착력을 증가시키기 위하여, 4-클로로벤젠티올(CBT)의 자기축합에 의한 PPS 중합시 c-MWNT를 함께 넣고 중합시킨 후 호모 PPS를 제거하여 MWNT-g-PPS를 얻었다. 이 MWNT-g-PPS의 열 및 표면 특성들을 분석하였으며, c-MWNT와 CBT가 반응하여 c-MWNT 표면에 PPS가 생성되었음을 확인하였다.

• 약학회지
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• 제50권6호
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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.

• Archives of Pharmacal Research
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• 제16권4호
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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.

• 약학회지
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• 제43권1호
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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)