CS260376B1 - 1-(4-benzoylphenyl)-3-chloropropane-1-on - Google Patents
1-(4-benzoylphenyl)-3-chloropropane-1-on Download PDFInfo
- Publication number
- CS260376B1 CS260376B1 CS873480A CS348087A CS260376B1 CS 260376 B1 CS260376 B1 CS 260376B1 CS 873480 A CS873480 A CS 873480A CS 348087 A CS348087 A CS 348087A CS 260376 B1 CS260376 B1 CS 260376B1
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- CS
- Czechoslovakia
- Prior art keywords
- benzoylphenyl
- chloropropan
- preparation
- compound
- chloropropane
- Prior art date
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- UQFKYXUHZBWDJQ-UHFFFAOYSA-N 1-(4-benzoylphenyl)-3-chloropropan-1-one Chemical compound C(C1=CC=CC=C1)(=O)C1=CC=C(C=C1)C(CCCl)=O UQFKYXUHZBWDJQ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- -1 1- (4-benzylphenyl) -3-chloropropan-1-one acetic acid Chemical compound 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- MCEIJDIUWXFKFR-UHFFFAOYSA-N 1-(4-benzylphenyl)-3-chloropropan-1-one Chemical compound C1=CC(C(=O)CCCl)=CC=C1CC1=CC=CC=C1 MCEIJDIUWXFKFR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- DULLEKOHORMWFS-UHFFFAOYSA-N 1-(4-benzoylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)C1=CC=CC=C1 DULLEKOHORMWFS-UHFFFAOYSA-N 0.000 description 1
- OLEDDXCAZXBUOG-UHFFFAOYSA-N 1-ethyl-4-(1-phenylethyl)benzene Chemical compound C1=CC(CC)=CC=C1C(C)C1=CC=CC=C1 OLEDDXCAZXBUOG-UHFFFAOYSA-N 0.000 description 1
- PHRVULSHEUYPRZ-UHFFFAOYSA-N 3-chloropropan-1-one Chemical compound ClCC[C]=O PHRVULSHEUYPRZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Riešenie sa týká novej zlúčeniny l-[4- -benzoylfenyl )-3-chlórpropán-l-ónu. Uvedená zlúčenina sa připraví tak, že k roztoku l-(4-benzylfenyl)-3-chlórpropán-l-ónu v kyselině octovej pri 30 °C sa přidává oxid chrómový. Zlúčenina má využitie pri príprave polymérov pre fotorezisty.The solution relates to the novel compound 1- [4- -benzoylphenyl) -3-chloropropan-1-one. Listed the compound is prepared so as to solution acid 1- (4-benzylphenyl) -3-chloropropan-1-one acetic acid is added at 30 ° C chromic. The compound has utility in preparation polymers for photoresists.
Description
Vynález sa týká l-( 4-benzoylf enyl)-3-chlórpropán-l-ónu.The invention relates to 1- (4-benzoylphenyl) -3-chloropropan-1-one.
Oxidácia benzylovej CH2 skupiny na ketón manganistanom draselným v přítomnosti kyseliny dusičnej a oxidu horečnatého vo vodnom prostředí sa využila i na přípravu aromatických 3-chlórpropán-l-ónov (P. Hrdlovič,. I. Lukáč „Developements in Polymer Degradation“ 4, 101 [1982], Ed. N. Grassie, Applied Science Publishers Ltd.). Výtažky sú však nízké. V literatúre je známa oxidácia l-fenyl-l-(4-etylfenyl)etánu s oxidom chrómovým v kyselině oetovej na l-(4-benzoylfenyl)-l-etanón v 85 %-nom výtažku (B. B. Corson, J. Dorsky, J. E. Nickels, W. M. Kutz, Η. I. Thaier, J. Org. Chem. 19, 17 [1954]). Preto pri přípravě 1-(4-benzoylf enyl j-3-chlórpropán-l-ónu sme postupovali podobné. 1- (4-benzoylfenyl)-3-chlórpropán-1-ón nie je popísaný v literatúre.Oxidation of the benzyl CH2 group to a ketone with potassium permanganate in the presence of nitric acid and magnesium oxide in an aqueous medium has also been used to prepare aromatic 3-chloropropan-1-one (P. Hrdlovic, I. Lukac "Developements in Polymer Degradation" 4, 101 [ 1982], Ed. N. Grassie, Applied Science Publishers Ltd.). However, the yields are low. It is known in the literature to oxidize 1-phenyl-1- (4-ethylphenyl) ethane with chromic oxide in oeto acid to 1- (4-benzoylphenyl) -1-ethanone in 85% yield (BB Corson, J. Dorsky, JE Nickels, WM Kutz, I. I. Thaier, J. Org. Chem. 19, 17 [1954]). Therefore, the preparation of 1- (4-benzoylphenyl) -3-chloropropan-1-one was similar and 1- (4-benzoylphenyl) -3-chloropropan-1-one is not described in the literature.
Podstatou vynálezu je l-( 4-benzoylf enyl)-3-chlórpropán-l-ón. SpQsob přípravy tejto zlúčeniny spočívá v tom, že k roztoku l-(4-benzylfenyl)-3-chlórpropán-l-ónu v kyselině oetovej pri 30 °G sa přidává oxid chrómový.The present invention provides 1- (4-benzoylphenyl) -3-chloropropan-1-one. A process for the preparation of this compound is to add chromium trioxide to a solution of 1- (4-benzylphenyl) -3-chloropropan-1-one in acetic acid at 30 ° C.
Výhodou uvedeného vynálezu je dobrý výtažok pripravovanej látky.An advantage of the present invention is a good yield of the preparation.
Hlavnou výhodou l-(4-benzoylfenyl)-3-chlórpropán-l-ónu oproti popísaným derivátem je, že dehydrochloráciou umožňuje připravit monomer s dvojitou vazbou, ktorý slúži k príprave špeciálnych polymérov využitelných pri príprave fotorezistov.The main advantage of 1- (4-benzoylphenyl) -3-chloropropan-1-one over the described derivatives is that by dehydrochlorination it is possible to prepare a double bond monomer which serves for the preparation of special polymers useful in the preparation of photoresists.
PříkladExample
Do miešaného rozteku l-(4-benzylfenylj-3-chlórpropán-l-ónu (22 g, 0,085 mólu) vTo a stirred solution of 1- (4-benzylphenyl) -3-chloropropan-1-one (22 g, 0.085 mol) in
1'adovej kyselině oetovej (195 ml) sa pomaly a opatrné přidává oxid chrómový (55 g, 0,55 mólu) tak, aby teplota bola tesne pod 30 °C. Pri 30 °C sa mieša ešte 4 hodiny, vyleje do 1 000 ml destilovanej vody pri 0 °C. Vytvořená zrazenina sa odfiltruje a po vysušení kryštalizuje z metanolu. V dalších experimentech sa použili na kryštalizáciu acetón a benzén. Získá sa 19,2 g (82,2%) bielej kryštalickej látky o t. t. 103 až 105 °C. Pre C16H13O2CI (272,73) vypočítané:Glacial acetic acid (195 ml) was added slowly and carefully with chromium trioxide (55 g, 0.55 mol) so that the temperature was just below 30 ° C. Stirring is continued at 30 ° C for 4 hours, poured into 1000 ml of distilled water at 0 ° C. The precipitate formed is filtered off and, after drying, crystallized from methanol. In further experiments acetone and benzene were used for crystallization. Yield: 19.2 g (82.2%) of white crystalline solid, m.p. 103-105 ° C. For C 16 H 13 O 2 Cl (272.73) calculated:
70,46 0/0 C, 4,80 % H, zistené:70.46% C, 4.80% H, found:
70,51 «/o C, 4,90 % H.70.51% C, 4.90% H.
IR (CCh : CHCb 2: 0,5):IR (CHCl3: CHCl3 2: 0.5):
640 (C—O), 1580 cm-1 (C—H aromatické).640 (C-O), 1580 cm -1 (C-H aromatic).
UV (CHCb):UV (CHCl3):
264 nm (log ε — 4,338),264 nm (log ε - 4,338),
331 nm (2,474).331 nm (2,474).
NMR (CDCb) í:NMR (CDCl3):
3,45 (t, 2H, CH2CI),3.45 (t, 2H, CH 2 Cl),
3,9 (t, 2H, CH2CO),3.9 (t, 2H, CH 2 CO),
7,75 (m, 9H, aromatické).7.75 (m, 9H, aromatic).
Mass m/e:Mass m / e:
272 (M+), 237, 236, 209, 197, 105.272 (M & lt ; + & gt ; ), 237, 236, 209, 197, 105.
Vynález má použitie v chemickom priemysle pri príprave nových polymérov využitelných prl príprave fotorezistov.The invention has application in the chemical industry in the preparation of new polymers useful in the preparation of photoresists.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873480A CS260376B1 (en) | 1987-05-14 | 1987-05-14 | 1-(4-benzoylphenyl)-3-chloropropane-1-on |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873480A CS260376B1 (en) | 1987-05-14 | 1987-05-14 | 1-(4-benzoylphenyl)-3-chloropropane-1-on |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS348087A1 CS348087A1 (en) | 1988-05-16 |
| CS260376B1 true CS260376B1 (en) | 1988-12-15 |
Family
ID=5375001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS873480A CS260376B1 (en) | 1987-05-14 | 1987-05-14 | 1-(4-benzoylphenyl)-3-chloropropane-1-on |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS260376B1 (en) |
-
1987
- 1987-05-14 CS CS873480A patent/CS260376B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS348087A1 (en) | 1988-05-16 |
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