• Archives of Pharmacal Research
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• 제15권2호
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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.

• Bulletin of the Korean Chemical Society
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• 제23권9호
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• pp.1213-1221
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• 2002

Friedel-Crafts alkylation reaction of an isomeric mixture of 1,2,3,4,5,6,7,8- (2) and 1,2,3,4,5,6,7,8-octahydrophenanthrene (2') with excess vinylchlorosilanes such as vinyl(methyl)dichlorosilane (1a) and vinyltrichlorosilane (1b) in the presence of aluminum chloride catalyst at 80 $^{\circ}C$ gives only one dialkylated products, 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthrenes [(Cl2XSiCH2CH2)2C14H16: X = Me (4a), Cl (4b)] in good yields, but 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydrophenanthrenes are not obtained. However, monoalkylation of 2 with 1 affords a mixture of both isomeric compounds, 9-[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthracenes 3 and -phenanthrenes 3'. The yield of product 3' is always higher than that of 3. When a mixture of 3 and 3' is alkylated again with 1, only product 4 without phenanthrene type compounds is obtained, indicating that the isomerizations between 2 and 2', or 3 and 3'occur under the alkylation condition. The alkylation with dimethylvinylchlorosilane or trimethylvinylsilane did not proceed. The structure of 4a is determined by X-ray single crystal diffraction analysis.

• Bulletin of the Korean Chemical Society
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• 제32권spc8호
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• pp.3130-3132
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• 2011

• 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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• 제38권5호
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• pp.504-510
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• 1994

A facile synthesis of 2-aryl-5-benzoxazolepropionic acid derivatives(1 0a-d), which are potent antiinflammatory agent, is reported. Methyl ${\alpha}$-(p-hydroxyphenyl)propionate(5) was prepared from Friedel-Crafts reaction of isopropoxy benzene with methyl ${\alpha}$-chloro-${\alpha}$-(methylthio) acetate(1), followed by desulfurization, methylation and clevage of ether bond. Compounds(10a-d) were made from(5) by a sequence of nitration, reduction, formation of benzoxazole ring, and hydrolysis in good yields, respectively.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.181.1-181.1
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• 2003

2-Aminoindan derivatives has been shown the serotonergic activities. In order to find new serotonergic agent, we trid to enlarge the indan ring. 3, 4-Dimethoxybenzaldehyde, used as starting material was condensed with malonic acid, piperidine to form 3, 4-dimethoxycinnamic acid. It was catalytically hydrogenated and sudsequently cyclized by Friedel-Crafts acylation reaction to yield 5, 6-dimethoxyindanone. This compound was reacted with pyrrolidine and then acrylamide to be synthesized the 3-membered ring. (omitted)

• 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.

• 약학회지
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• 제32권5호
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• pp.340-342
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• 1988

New synthetic method for ibuprofen, which is a potent antiinflammatory agent, was described. Ethyl ${\alpha}-methylthio-p-isobutylphenylacetate$ was obtained from Friedel-Crafts reaction of isobutylbenzene with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ in the presence of $SnCl_4$. Ibuprofen was prepared in good yield by treatment of ethyl ${\alpha}-methylthio-p-isobutylphenylacetate$ with NaH and MeI, followed by desulfurization with zinc dust-acetic acid and hydrolysis of the resultant ethyl 2-methylthio-2-(4-isobutylphenyl)propionate.

• Korean Membrane Journal
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• 제4권1호
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• pp.20-24
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• 2002

The surface of polysulfone membranes has been modified using the fluorine chemicals, ITFE (2-iodo-1,1,1-trifluoro-ethane F.W.=209.94) and PFPI (1H,1H-pentafluoro-n-propyl iodide F.W.=259.95), and PFI (1H,1H,2H,2H-perfluorohexyl iodide, F.W.=373.99) based on Friedel-Crafts reaction mechanism with varying reaction temperatures, reaction time, and catalysis types. The resulting membranes were characterized through mainly the contact angle measurement and pure water permeability. The smaller reactant shows the larger contact angles. FeBr$_3$ catalyst is more effective than AlCl$_3$. Typically, the PS film treated with ITFE at $25^{\circ}C$ under FeBr$_3$ catalyst showed the contact angle 78.5$^{\circ}C$ which indicated 10% over the value of unreacted PS films. More than 50% of pure water flux 8.0 g/$m^2$hr, reduced at reaction time 10 min relative to the original flux, 3.49 g/$m^2$hr.

• Archives of Pharmacal Research
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• 제17권3호
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• pp.190-193
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• 1994

Friedel-Crafts reaction isopropoxybenzene with methyl $\alpha$-chloro-$\alpha$-(maethylthio)acetate 1 afforded methyl $\alpha$-methylthio-p-isopropoxyphenylacetate 2d, which was readily converted into methyl p-isopropoxyphenylacetate 3 by reductive desulfurization with zinc dust in acetic acid. Methylation of 3 with sodium hydride and methyl iodide gave methyl $\alpha$-(p-isopropoxyphenyl)propionate 5. Methyl p-hydroxyphenylakanoates (4,6), useful intermediates for some medicines, were easily prepared by treatment of 3 and 5 with titanium tetrachloride, respectively.