CS276059B6 - 1- (4-benzoylphenyl) -1- (4- (3-chloropropanesyl) phenyl) methane - Google Patents
1- (4-benzoylphenyl) -1- (4- (3-chloropropanesyl) phenyl) methane Download PDFInfo
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- CS276059B6 CS276059B6 CS902360A CS236090A CS276059B6 CS 276059 B6 CS276059 B6 CS 276059B6 CS 902360 A CS902360 A CS 902360A CS 236090 A CS236090 A CS 236090A CS 276059 B6 CS276059 B6 CS 276059B6
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Abstract
Riešenie ee týká novej zlúčeniny l-(4-benzoylfenyl)-l-(4-(3-chlórpropanoyl)fenyl) metánu. Uvedená zlúčenina ea připraví tak, že na zmes 3-chlórpropanoylchlorldu a bezvodého chloridu hlinitého v chloride uhllčltom sa pósobi l-(4-benzoylfenyl)-l-fenylmetánom. Zlúčenina Je medzlproduktom pripravy monomérov vhodných na přípravu polymérnych svetlom degradovatelných materiálov.Solution ee relates to a new compound 1-(4-benzoylphenyl)-1-(4-(3-chloropropanoyl)phenyl) methane. Said compound ea is prepared by treating a mixture of 3-chloropropanoyl chloride and anhydrous aluminum chloride in carbon tetrachloride with 1-(4-benzoylphenyl)-1-phenylmethane. The compound is an intermediate in the preparation of monomers suitable for the preparation of polymeric photodegradable materials.
Description
Vynález ea týká l-(4-benzoylfenyl)-l-(4-(3-chlórpropanoyl)-fenyl) metánu.The invention relates to 1- (4-benzoylphenyl) -1- (4- (3-chloropropanoyl) phenyl) methane.
Hriadel - Craftsova acylácla aromatických látok je obecnou metódou prlpravy aromatických ketónov. Acylácla difenylmetánu a acetylchlorldom i a benzoylchloridom v přítomnosti bezvodého chloridu hlinitého je poplaaná (D.T.Mowry, M.Renoll, W.F.Huber, 3. Amer, Chem.Shaft - Crafts acylation of aromatic compounds is a general method for the preparation of aromatic ketones. Acylation of diphenylmethane and acetylchloride 1 with benzoyl chloride in the presence of anhydrous aluminum chloride is discussed (D. T.Mowry, M. Renoll, W. F. Hub, 3. Amer, Chem.
Soc. 68.1105 (1946) a D.A.McCombe, C.S.Menon, 3.Higgine, 3, Polymer Sci,:Part A-1,9,1261 (1971). Doteraz však nebol l-(4-benzoylfenyl)-l-(4-(3-chlórpropanoyl)fenyl) metón připravený.Soc. 68, 1105 (1946) and D. A. McCombe, C. S. Menen, 3. Higgine, 3, Polymer Sci,: Part A-1,9,1261 (1971). However, to date, 1- (4-benzoylphenyl) -1- (4- (3-chloropropanoyl) phenyl) methone has not been prepared.
Podstatou vynálezu Je l-(4-benzoylfenyl)-l-(4-(3-chlórpropanoyl)fenyl) metán. Sposob prlpravy tejto zlúčeniny spočiva v tom, že na zmes 3-chlórpropanoylchloridu a bezvodého chloridu hlinitého v chloride uhličitom ee poeobi l-(4-benzoylfenyl)-l-fenylmetánom.The present invention provides 1- (4-benzoylphenyl) -1- (4- (3-chloropropanoyl) phenyl) methane. The process for the preparation of this compound is that 1- (4-benzoylphenyl) -1-phenylmethane is added to a mixture of 3-chloropropanoyl chloride and anhydrous aluminum chloride in carbon tetrachloride.
Uvedený postup umožňuje připravil predmetnú zlúčeninu poměrně Jednoducho vo výtažku 63 %. Přiklad K miešanej zmesi bezvodého chloridu hlinitého (22,4 g, 0,166 molu) a chloridu uhličitého (20 ml) ea pri teplote 0 až 5 °C prldé 3-chlórpropanoylchlorid (11 ml, 0,114 mól). Pri rovnakej teplote ea po kvapkéch prldé roztok l-(4-benzoylfenyl)-l-fenylnetánu (20 g, 0,73 mólu) v chloride uhličitom (68 ml). Po přidáváni ee zmea mieša ešte 30 min. pri teplote mieetnoeti, vyleje po častiach do etudenej vody okyelenej kyselinou chlorovodíkovou a extrahuje chloroformom. Státlm zahuštěného extraktu v chladnička vznikly velké kryštály, ktoré po opláchnuti hexénom a opatrné dietyléterom a benzénom vážili 19,9 g. Po chromatografickom čištěni na silikegéle e eluentom benzén : hexénu 7 : 3 sa ziska 16,6 g (63 %) bielej kryštalickej látky, ktoré po kryštalizácii z benzénu má t.t. 86 až 88 °C„ Pre C23H19°2C^ (362,86) vypočítané; 76,13% C, 5,28% Hj nájdené: 75,88% C, 5,32% H. IC spektrum (CC14: CHC13 Ijl): 1660 a 1680 cm"* (OO). UV spektrum (CH&3): 263 nm (10g£>· 4,52): 333 nm (2,50). 1H NMR spektrum: Γ- 3,43 (t, 2H, -CHg-C-O); 3,91 (t, 2H. -CH2Cl)j 4,11 (β, 2H. -CHg” medzi Jadraml); 7,25-7,35 (m, 4H, arom, o” k CHg)t 7-42-7,50 (m, 2H, arom. na fenyle »" k OO) j 7,53-7,60 (a, 1H, arom, na fenyXe p“ k OO): 7,71-7,81 (m, 4H, arom. o" k OO na disubstituovanýeh Jadrách): 7,87-7,93 (m, 2H, arom. o” k C«0 na fenyle). Hmotnostní spektrum: m/e 362 (M+), 326, 299, 249, 165, 105, 77.Said process makes it possible to prepare the compound in question relatively simply in a yield of 63%. Example To a stirred mixture of anhydrous aluminum chloride (22.4 g, 0.166 mol) and carbon tetrachloride (20 ml) and at 0 to 5 ° C was added 3-chloropropanoyl chloride (11 ml, 0.114 mol). At the same temperature and dropwise, a further solution of 1- (4-benzoylphenyl) -1-phenylnetane (20 g, 0.73 mol) in carbon tetrachloride (68 mL). After addition, the mixture was stirred for 30 min. at room temperature, poured portionwise into ice-water acidified with hydrochloric acid and extracted with chloroform. Large thickened crystals were formed in the refrigerator and thickened with hexene and cautiously with diethyl ether and benzene. After chromatographic purification on silica gel eluent, benzene: hexene 7: 3, 16.6 g (63%) of a white crystalline solid were obtained. which after crystallization from benzene has tt 86-88 ° C "For C 23 H 19 O 2 (362.86) calculated; H, 5.28; Found: C, 75.88; H, 5.32; IC spectrum (CCl4: CHCl3, II): 1660 and 1680 cm @ -1 (OO). ): 263 nm (10 g, ≥ 4.52): 333 nm (2.50), 1 H NMR Spectrum: δ-3.43 (t, 2H, -CH 3 -CO), 3.91 (t, 2H). 4.11 (β, 2H, -CHg 'between Jadraml); 7.25-7.35 (m, 4H, arom, o' to CH2) t 7-42-7.50 (m, 2H , aromatic on phenyl »OO is 7.53-7.60 (a, 1H, arom, on phenylXe p 'to OO): 7.71-7.81 (m, 4H, arom. OO to disubstituted nuclei): 7.87-7.93 (m, 2H, aromatic o to C10 on phenyl) Mass spectrum: m / e 362 (M +), 326, 299, 249, 165, 105 , 77.
Vynález má použitie v chemickom priemysle. Předmětná látka je medziproduktom k přípravě monomárov pre pripravu polymárnych svetlom degradovatelných materiálov.The invention has utility in the chemical industry. The subject matter is an intermediate for preparing monomers for preparing polymeric light degradable materials.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS902360A CS276059B6 (en) | 1990-05-15 | 1990-05-15 | 1- (4-benzoylphenyl) -1- (4- (3-chloropropanesyl) phenyl) methane |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS902360A CS276059B6 (en) | 1990-05-15 | 1990-05-15 | 1- (4-benzoylphenyl) -1- (4- (3-chloropropanesyl) phenyl) methane |
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| Publication Number | Publication Date |
|---|---|
| CS236090A3 CS236090A3 (en) | 1992-01-15 |
| CS276059B6 true CS276059B6 (en) | 1992-03-18 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS902360A CS276059B6 (en) | 1990-05-15 | 1990-05-15 | 1- (4-benzoylphenyl) -1- (4- (3-chloropropanesyl) phenyl) methane |
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| CS236090A3 (en) | 1992-01-15 |
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