CS260376B1 - 1- (4-benzoylphenyl) -3-chloropropan-1-one - Google Patents
1- (4-benzoylphenyl) -3-chloropropan-1-one Download PDFInfo
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- 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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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 concerns the new compound 1-[4-benzoylphenyl)-3-chloropropan-1-one. The mentioned compound is prepared by adding chromium oxide to a solution of 1-(4-benzylphenyl)-3-chloropropan-1-one in acetic acid at 30°C. The compound is used in the preparation of 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-chloropropan-1-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873480A CS260376B1 (en) | 1987-05-14 | 1987-05-14 | 1- (4-benzoylphenyl) -3-chloropropan-1-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS348087A1 CS348087A1 (en) | 1988-05-16 |
| CS260376B1 true CS260376B1 (en) | 1988-12-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS873480A CS260376B1 (en) | 1987-05-14 | 1987-05-14 | 1- (4-benzoylphenyl) -3-chloropropan-1-one |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS260376B1 (en) |
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1987
- 1987-05-14 CS CS873480A patent/CS260376B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS348087A1 (en) | 1988-05-16 |
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