CS266111B1 - 2- (4-benzoylphenyl) -2- (4-propenoylfenyl) propane - Google Patents
2- (4-benzoylphenyl) -2- (4-propenoylfenyl) propane Download PDFInfo
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- CS266111B1 CS266111B1 CS875527A CS552787A CS266111B1 CS 266111 B1 CS266111 B1 CS 266111B1 CS 875527 A CS875527 A CS 875527A CS 552787 A CS552787 A CS 552787A CS 266111 B1 CS266111 B1 CS 266111B1
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- benzoylphenyl
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- propenoylfenyl
- acetonitrile
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Abstract
Riešenie sa týká novej zlúčeniny 2—(4— -benzoylfenyl)-2-(4-propenoyl)propánu. Uvedená zlúčenina sa připraví tak, že na 2-(4-benzoylfenyl)-2-C4-(3-chlórpropanoyl)- fenyljpropán sa pósobí octanom sodným v acetonitrile pri 50 °C. Zlúčenina je monomérom k príprave polymérov degradujúcich světlom.The solution relates to a new compound 2-(4-benzoylphenyl)-2-(4-propenoyl)propane. The compound is prepared by treating 2-(4-benzoylphenyl)-2-C4-(3-chloropropanoyl)phenylpropane with sodium acetate in acetonitrile at 50 °C. The compound is a monomer for the preparation of photodegradable polymers.
Description
(57) Riešenie sa týká novej zlúčeniny 2—(4— -benzoylfenyl)-2-(4-propenoyl)propánu. Uvedená zlúčenina sa připraví tak, že na 2-(4-benzoylfenyl)-2-C4-(3-chlórpropanoyl)fenyljpropán sa pósobí octanom sodným v acetonitrile pri 50 °C. Zlúčenina je monomérom k príprave polymérov degradujúcich světlom. 266111 (11) (13) bi (51) Int. Cl.4 C 07 C 49/796 CS 266111 Bl 2 CS 266 111 Bl(57) The present invention relates to a novel compound 2- (4-benzoylphenyl) -2- (4-propenoyl) propane. The compound is prepared by treating 2- (4-benzoylphenyl) -2-C4- (3-chloropropanoyl) phenylpropane with sodium acetate in acetonitrile at 50 ° C. The compound is a monomer for preparing light-degrading polymers. 266111 (11) (13) (51) Int. Cl.4 C 07 C 49/796 EN 266111 Bl 2 EN 266 111 Bl
Vynález sa týká 2-(4-benzoylfenyl)-2-(4-propenoylfenyl)propánu.The invention relates to 2- (4-benzoylphenyl) -2- (4-propenoylphenyl) propane.
Aromatické vinylketóny sa pripravujú obecne dehydrochloráciou l-aryl-3-chlór-l-propanónov (P. Hrdlovič, I. Lukáč, "Developements in Polymer Degradation" 4, 101,1982, Ed. N. Grassie, Applied Science Publishers Ltd.). Rovnaká metoda sa použila i na pripravu 2-(4-benzoylfenyl)-2-(4-propenoylfenyl)propánu, ktorý nie je popísaný v literatúre.Aromatic vinyl ketones are generally prepared by dehydrochlorination of 1-aryl-3-chloro-1-propanones (P. Hrdlovič, I. Lukáč, " Developements in Polymer Degradation " . The same method was used to prepare 2- (4-benzoylphenyl) -2- (4-propenoylphenyl) propane, which is not described in the literature.
Podstatou vynálezu je 2-(4-benzoylfenyl)-2-(4-propenoylfenyl)propán. Spůsob přípravy tejto zlúčeniny spočívá v tom, že na 2-(4-benzoylfenyl)-2-C4-(3-ohlórpropanoyl)fenyljpropán sa působí octanom sodným v acetonitrile pri 50 °C. Výhodou uvedeného vynálezu je, že umožňuje připravit predmetnú zlúčeninu vo vysokom výtažku a jednoducho. Předmětná zlúčenina je monomérom k príprave polymérov degradujúcich svetlom. PříkladThe subject of the invention is 2- (4-benzoylphenyl) -2- (4-propenoylphenyl) propane. The process for preparing this compound is to treat 2- (4-benzoylphenyl) -2-C4- (3-fluoropropanoyl) phenylpropane with sodium acetate in acetonitrile at 50 ° C. It is an advantage of the present invention that it makes it possible to prepare the subject compound in high yield and simply. The subject compound is a monomer for preparing light-degrading polymers. Example
Roztok 2-(4-benzoylfenyl)-2-C4-(3-chlórpropanoyl)fenyljpropánu (30,7 g, 0,078 mol) v acetonitrile (50 ml) sa přidá po častiach k miešanej suspenzii octanu sodného (39,5 g, 0,4 mól) v acetonitrile (550 ml). Po miešaní 1 h pri 50 °C produkt podlá chromatografie neobsahuje východziu látku. Reakčná zmes sa neutralizuje roztokom uhličitanu sodného (8,21 g, 0,078 mol) vo vodě (70 ml) a extrahuje dietyléterom. Extrakt sa suší bezvodým síranom sodným a zahustí za vákua. Získá sa 22,7 g (82 hmot %) žltej viskóznej kvapaliny. Analytická vzorka sa získá chromatografický (silikagél L 100/400, eluent n-hexán:aceton 9:1). Elementárna analýza pre C25H22O2 (354,45) vypočítané: 84,71 hmot. % uhlíka, 6,26 hmot. % vodíka, nájdené: 84,59 hmot. % uhlíka, 6,34 hmot. % vodíka. IR CC14: 1 680 (C=O), 1 670 (C=O), 1 605 cm-1 (C-H aromatické). UV CHCl-j: 267 nm (logf= 5,83), 340 (2,49). 1H NMR (CDCl.,) : 1,75 (s, 6H,A solution of 2- (4-benzoylphenyl) -2-C4- (3-chloropropanoyl) phenylpropane (30.7 g, 0.078 mol) in acetonitrile (50 ml) was added portionwise to a stirred suspension of sodium acetate (39.5 g, 0%). , 4 mol) in acetonitrile (550 mL). After stirring for 1 h at 50 ° C, the chromatography does not contain the starting material. The reaction mixture was neutralized with a solution of sodium carbonate (8.21 g, 0.078 mol) in water (70 mL) and extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate and concentrated in vacuo. 22.7 g (82%) of a yellow viscous liquid are obtained. An analytical sample is obtained by chromatography (silica gel L 100/400, eluent n-hexane: acetone 9: 1). Elemental analysis calculated for C25H22O2 (354.45): 84.71 wt. % carbon, 6.26 wt. % hydrogen, found: 84.59 wt. % carbon, 6.34 wt. % hydrogen. IR CCl 4: 1680 (C = O), 1670 (C = O), 1665 cm -1 (C-H aromatic). UV CHCl 3: 267 nm (logf = 5.83), 340 (2.49). 1 H NMR (CDCl 3): 1.75 (s, 6H,
CH3), 5,83, 5,85, 5,94, 5,96 (2xd, 1H, H-C=C trans), 6,32, 6,34, 6,49, 6,51 (2xd, 1H, H-C=C cis), 7,02, 7,12, 7,19 (m, 0,85 H, =CH-CO), 7,28 až 7,59 (m, 7H, aromatické + 0,15H, =CH-CO-), 7,64 až 7,93 (m, 6H, aromatické orto k C=O). Hmotnostně spektrum m/e: 354 (M+), 339, 327, 223, 178, 105, 77.CH3), 5.83, 5.85, 5.94, 5.96 (2xd, 1H, HC = C trans), 6.32, 6.34, 6.49, 6.51 (2xd, 1H, HC) = C cis), 7.02, 7.12, 7.19 (m, 0.85 H, = CH-CO), 7.28 to 7.59 (m, 7H, aromatic + 0.15H, = CH -CO-), 7.64 to 7.93 (m, 6H, aromatic ortho to C = O). Mass Spectrum m / e: 354 (M +), 339, 327, 223, 178, 105, 77.
Vynález má využitie v chemickom priemysle pri príprave polymérov vyznačujúcich sa vysokou degradácioui ultrafialovým svetlom.The invention has utility in the chemical industry for the preparation of polymers characterized by high ultraviolet light degradation.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875527A CS266111B1 (en) | 1987-07-22 | 1987-07-22 | 2- (4-benzoylphenyl) -2- (4-propenoylfenyl) propane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875527A CS266111B1 (en) | 1987-07-22 | 1987-07-22 | 2- (4-benzoylphenyl) -2- (4-propenoylfenyl) propane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS552787A1 CS552787A1 (en) | 1989-03-14 |
| CS266111B1 true CS266111B1 (en) | 1989-11-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS875527A CS266111B1 (en) | 1987-07-22 | 1987-07-22 | 2- (4-benzoylphenyl) -2- (4-propenoylfenyl) propane |
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| Country | Link |
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| CS (1) | CS266111B1 (en) |
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1987
- 1987-07-22 CS CS875527A patent/CS266111B1/en unknown
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| Publication number | Publication date |
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| CS552787A1 (en) | 1989-03-14 |
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