BE574140A - - Google Patents
Info
- Publication number
- BE574140A BE574140A BE574140DA BE574140A BE 574140 A BE574140 A BE 574140A BE 574140D A BE574140D A BE 574140DA BE 574140 A BE574140 A BE 574140A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- endomethylene
- reaction
- tetrahydrophthalane
- hexachloro
- Prior art date
Links
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000001491 aromatic compounds Chemical class 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 140
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000000460 chlorine Substances 0.000 description 20
- 239000000155 melt Substances 0.000 description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- -1 methoxy compound Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ARPANWHHRGVXBN-UHFFFAOYSA-N 1,2,3,4,4a,10-hexahydroanthracene Chemical class C1=CC=C2CC(CCCC3)C3=CC2=C1 ARPANWHHRGVXBN-UHFFFAOYSA-N 0.000 description 1
- 101700042999 ALLC Proteins 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 241001633942 Dais Species 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N Diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 241001190717 Hea Species 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N M-Xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001464 adherent Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002146 bilateral Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE574140A true BE574140A (pl) |
Family
ID=190723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE574140D BE574140A (pl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE574140A (pl) |
-
0
- BE BE574140D patent/BE574140A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0248734B1 (fr) | Dérivés de benzo[b]thiophène et benzo[b]furannecarboxamides, leurs procédés de préparation et les médicaments les contenant | |
| EP0001534B1 (fr) | Nouveaux dérivés du pyrrole, leur procédé de préparation et leurs applications en thérapeutique | |
| EP1315709A1 (fr) | Aminoalkykbenzoyl-benzofuranes ou benzothiophenes, leur procede de preparation et les compositions les contenant | |
| BE574140A (pl) | ||
| EP0000453A1 (fr) | Procédé de préparation de dérivés de la thiénopyridine | |
| CH640537A5 (fr) | Procede de preparation de 3-exomethylenecepham-sulfoxydes. | |
| EP0080419B1 (fr) | Haloalkyl-8-4H-(1)-benzopyran-4-ones, et procédés de préparation | |
| EP0151052B1 (fr) | Aminoéthylimidazole, composition pharmaceutique en contenant et procédé de préparation | |
| CH392483A (fr) | Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques | |
| WO1995030660A1 (fr) | Procede pour la preparation de pyrazines substituees | |
| CH594650A5 (en) | Antiinflammatory (1,2)-benzothiazine derivs. prepn. | |
| EP0414686B1 (fr) | Derives de trifluoromethyl-1-tetralines, leur preparation et leur application pour la synthese de composes presentant des proprietes therapeutiques | |
| EP0184957B1 (fr) | -N-méthyl(méthyl-6 pyridyl-2)-2 dithianne-1,3 carbothioamide-2, sa préparation et les médicaments qui la contiennent | |
| WO1992021665A1 (fr) | Nouveaux derives de l'oxazole et leur preparation | |
| EP0027085B1 (fr) | Nouveaux dérivés de la thiazolo (3,2-c) benzoxazine-1,3, leur préparation et les médicaments qui les contiennent | |
| EP0228356B1 (fr) | Nouveaux dérivés d'hydroxy-4 indole, leur procédé de préparation et leur utilisation | |
| FR2475541A1 (fr) | Nouveaux intermediaires de synthese de colorants | |
| FR2487825A1 (fr) | Procede de preparation d'esters d'acides acylazo-3 propioniques | |
| CA1044697A (fr) | Procede de preparation de nouveaux azabicycloalcanes disubstitues | |
| BE529377A (pl) | ||
| BE504409A (pl) | ||
| BE522244A (pl) | ||
| BE482075A (pl) | ||
| BE571842A (pl) | ||
| BE569076A (pl) |