CS266113B1 - 2-/4-benzoylphenyl/-2-/4-/3-chloropropanoyl/phenyl/propane - Google Patents
2-/4-benzoylphenyl/-2-/4-/3-chloropropanoyl/phenyl/propane Download PDFInfo
- Publication number
- CS266113B1 CS266113B1 CS875529A CS552987A CS266113B1 CS 266113 B1 CS266113 B1 CS 266113B1 CS 875529 A CS875529 A CS 875529A CS 552987 A CS552987 A CS 552987A CS 266113 B1 CS266113 B1 CS 266113B1
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- CS
- Czechoslovakia
- Prior art keywords
- benzoylphenyl
- chloropropanoyl
- propane
- phenyl
- chloride
- Prior art date
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 5
- 239000001294 propane Substances 0.000 title claims description 5
- -1 2- (4-benzoylphenyl) -2- [4- (3-chloropropanoyl) phenyl] propane Chemical compound 0.000 claims abstract description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 abstract description 3
- MMTMIDUCLXIEQH-UHFFFAOYSA-N phenyl-[4-(2-phenylpropan-2-yl)phenyl]methanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 MMTMIDUCLXIEQH-UHFFFAOYSA-N 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 2
- 230000000593 degrading effect Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Riešenie sa týká novej zlúčeniny 2—(4— -benzoylfenyl)-2-t4-(3-chlórpropanoyl)fenyll- propánu. Uvedená zlúčenina sa připraví tak, že na 3-chlórpropanoylchlorid v chloride uhličitom v přítomnosti bezvodého chloridu hlinitého sa pósobí 2-<4-benzoylfenyl)-2-fenyl- propánom. Předmětná látka je medziproduktom pre přípravu monoméru a svetlom degradujúcich polymérov.The present invention relates to a novel compound 2- (4-benzoylphenyl) -2- [4- (3-chloropropanoyl) phenyl] propane. The compound is prepared by treating 3-chloropropanoyl chloride in carbon tetrachloride in the presence of anhydrous aluminum chloride with 2- (4-benzoylphenyl) -2-phenylpropane. The subject matter is an intermediate for preparing monomer and light degrading polymers.
Description
Vynález sa týká 2-(4-benzoylfenyl)-2-C4-Í3-chlórpropanoyl)fenyljpropánu.The present invention relates to 2- (4-benzoylphenyl) -2-C4- (3-chloropropanoyl) phenyl] propane.
Popísaná je příprava di-2-(4-acetylfenyl)propánu Friedel-Craftsovou acyláciou 2,2-difenylpropánu (Ε. I. du Pont, GB pat. 753 384, Chem. Abstr. 53, 1 253f, 1958, I. L. Kotlyarevskii, A. S. Zanina, N. M. Gusenkova, Izv. Akad. Nauk ZSSR, Ser. Khim 1967, 900). 2—(4— -benzoylfenyl)-2-C4-(3-chlórpropanoyl)fenyljpropán nie je popísaný v literatúre.Described is the preparation of di-2- (4-acetylphenyl) propane by Friedel-Crafts acylation of 2,2-diphenylpropane (E.I. du Pont, GB Pat. 753,384, Chem. Abstr. 53, 1253f, 1958, IL Kotlyarevskii, AS Zanina, NM Gusenkova, Izv. Akad Nauk USSR, Ser. Khim 1967, 900). 2- (4-Benzoylphenyl) -2-C4- (3-chloropropanoyl) phenyl] propane is not described in the literature.
Podstatou vynálezu je 2-(4-benzoylfenyl)-2-E4-(3-chlórpropanoyl)fenyljpropán. Spósob přípravy tejto zlúčeniny spočívá v tom, že na 3-chlórpropanoylohlorid v chloride uhličitom v přítomnosti bezvodého chloridu hlinitého sa pósobí 2-(4-benzoylfenyl)-2-fenylpropánom napřed pri teplote nižšej ako 5 °C a neskoršie pri 20 °C počas 30 minút.The present invention provides 2- (4-benzoylphenyl) -2-E4- (3-chloropropanoyl) phenyl] propane. A method for the preparation of this compound is to treat 3-chloropropanoyl chloride in carbon tetrachloride in the presence of anhydrous aluminum chloride with first 2- (4-benzoylphenyl) -2-phenylpropane at a temperature below 5 ° C and later at 20 ° C for 30 minutes. minutes.
Výhodou uvedeného vynálezu je, že umožňuje připravit jednoducho predmetnú zlúčeninu v 30 %-nom výtažku.An advantage of the present invention is that it makes it possible to prepare a simple object compound in a 30% yield.
Předmětná látka je medziproduktom pre přípravu monomeru a svetlom degradujúcich polymérov .The present substance is an intermediate for the preparation of monomer and light-degrading polymers.
PříkladExample
K suspenzií bezvodého chloridu hlinitého (31,2 g, 0,234 mol) v chloride uhličitom (60 ml) sa pri 0 °C přidá 3-chlórpropanoyl-chlorid (15 ml, 0,16 mol). Po kvapkách sa přidá roztok 2-(4-benzoylfenyl)-2-fenylpropánu (30 g, 0,1 mól) v chloride uhličitom (60 ml) tak, aby teplota nevystúpila nad 5 °C. Po přidaní sa zmes mieša 30 minút pri 20 °C, vyleje opatrné do roztoku kyseliny chlorovodíkovéj (10 ml) vo vodě (400 ml), extrahuje chloroformom a extrakt sa zahustí pri zníženom tlaku. Po chromatografickom delení na silikagéle L 100/400 s eluentom benzén: h-hexán 9:1 a zahuštěni sa získá nažltlá viskózna kvapalina (11,7 g, 30 hmot. %). Elementárna analýza pre C25H23°2C1· (390,91) vypočítané: 76,81 hmot. % uhlík, 5,93 hmot. % vodík, nájdené: 77,30 hmot. % uhlík, 6,17 hmot. % vodík. IR (CC14): 1 690 (C=0), 1 660 (C=O), 1 600 cm1 (C=H, aromatické). UV (CHClj): 260 nm (log£= 4,55), 335 (3,0). 1H NMR (CDC13) : 1,63 (s, 6H, CH3), 3,16 až 3,48 (t, 2K, -CHjCO-), 3,65 až 3,90 (t, 2H, -CH2C1), 7,09 až 7,9 (m, 13H, aromatické).To a suspension of anhydrous aluminum chloride (31.2 g, 0.234 mol) in carbon tetrachloride (60 mL) at 0 ° C was added 3-chloropropanoyl chloride (15 mL, 0.16 mol). A solution of 2- (4-benzoylphenyl) -2-phenylpropane (30 g, 0.1 mol) in carbon tetrachloride (60 mL) was added dropwise such that the temperature did not rise above 5 ° C. After the addition, the mixture was stirred at 20 ° C for 30 minutes, poured carefully into a solution of hydrochloric acid (10 mL) in water (400 mL), extracted with chloroform, and the extract was concentrated under reduced pressure. Chromatography on silica gel L 100/400 with 9: 1 benzene: h-hexane and concentration gives a yellowish viscous liquid (11.7 g, 30 wt%). Elemental analysis for C 25 H 23 ° 2 Cl · (390.91) calculated: 76.81 wt. % carbon, 5.93 wt. % hydrogen, found: 77.30 wt. % carbon, 6.17 wt. % hydrogen. IR (CCl4): 1690 (C = O), 1660 (C = O), 1600 cm @ -1 (C = H, aromatic). UV (CHCl 3): 260 nm (log δ = 4.55), 335 (3.0). 1 H NMR (CDCl 3): 1.63 (s, 6H, CH 3 ), 3.16-3.48 (t, 2K, -CH 3 CO-), 3.65-3.90 (t, 2H, -CH 2 Cl), 7.09 to 7.9 (m, 13H, aromatic).
Vynález má použitie v chemickom priemysle pri príprave polymérov vyznačujúcich sa vysokou degradáciou ultrafialovým svetlom.The invention has application in the chemical industry in the preparation of polymers characterized by high degradation by ultraviolet light.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875529A CS266113B1 (en) | 1987-07-22 | 1987-07-22 | 2-/4-benzoylphenyl/-2-/4-/3-chloropropanoyl/phenyl/propane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875529A CS266113B1 (en) | 1987-07-22 | 1987-07-22 | 2-/4-benzoylphenyl/-2-/4-/3-chloropropanoyl/phenyl/propane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS552987A1 CS552987A1 (en) | 1989-03-14 |
| CS266113B1 true CS266113B1 (en) | 1989-11-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS875529A CS266113B1 (en) | 1987-07-22 | 1987-07-22 | 2-/4-benzoylphenyl/-2-/4-/3-chloropropanoyl/phenyl/propane |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS266113B1 (en) |
-
1987
- 1987-07-22 CS CS875529A patent/CS266113B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS552987A1 (en) | 1989-03-14 |
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