NO885591L - Fremgangsmaate for fremstilling av substituerte aromatiskeforbindelser. - Google Patents

Fremgangsmaate for fremstilling av substituerte aromatiskeforbindelser.

Info

Publication number: NO885591L
Authority: NO; Norway
Prior art keywords: group; stated; ether; mmol; reaction
Prior art date: 1987-12-18

Application number

NO88885591A

Other languages

English (en)

Norwegian (no)

Other versions

NO885591D0 (no

Inventor

Thomas Tod Hudec

Original Assignee

Norwich Eaton Pharma

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-12-18

Filing date

1988-12-16

Publication date

1989-06-19

1988-12-16 Application filed by Norwich Eaton Pharma filed Critical Norwich Eaton Pharma

1988-12-16 Publication of NO885591D0 publication Critical patent/NO885591D0/no

1989-06-19 Publication of NO885591L publication Critical patent/NO885591L/no

Links

238000000034 method Methods 0.000 title claims abstract description 29
150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims abstract description 23
150000001875 compounds Chemical class 0.000 claims abstract description 21
239000002904 solvent Substances 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 6
239000003054 catalyst Substances 0.000 claims abstract description 5
239000000126 substance Substances 0.000 claims abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 55
125000004432 carbon atom Chemical group C* 0.000 claims description 14
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 13
229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 13
239000001119 stannous chloride Substances 0.000 claims description 13
235000011150 stannous chloride Nutrition 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
-1 cyclic acetal Chemical class 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract description 4
125000001931 aliphatic group Chemical group 0.000 abstract description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
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 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 27
239000000203 mixture Substances 0.000 description 24
239000010410 layer Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
239000000047 product Substances 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
WZBQFNAWQPYQPM-UHFFFAOYSA-N hex-5-ynoyl chloride Chemical compound ClC(=O)CCCC#C WZBQFNAWQPYQPM-UHFFFAOYSA-N 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
229910052786 argon Inorganic materials 0.000 description 6
239000012043 crude product Substances 0.000 description 6
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical group OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 6
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 4
238000005727 Friedel-Crafts reaction Methods 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
DJPAQOCIUDXBHK-UHFFFAOYSA-N 2,4-dibromo-6-(trifluoromethyl)phenol Chemical compound OC1=C(Br)C=C(Br)C=C1C(F)(F)F DJPAQOCIUDXBHK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
150000007970 thio esters Chemical class 0.000 description 3
QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical class CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 2
SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical class CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 2
IIBWBAUXZPOXIZ-UHFFFAOYSA-N 2-bromo-6-(trifluoromethyl)phenol Chemical compound OC1=C(Br)C=CC=C1C(F)(F)F IIBWBAUXZPOXIZ-UHFFFAOYSA-N 0.000 description 2
PISMFZKNXHOJFO-UHFFFAOYSA-N 2-methyl-6-(trifluoromethyl)phenol Chemical compound CC1=CC=CC(C(F)(F)F)=C1O PISMFZKNXHOJFO-UHFFFAOYSA-N 0.000 description 2
BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 2
JHCFLUGYQKACEJ-UHFFFAOYSA-N 2-tert-butyl-6-prop-2-enylphenol Chemical compound CC(C)(C)C1=CC=CC(CC=C)=C1O JHCFLUGYQKACEJ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
MAHPVQDVMLWUAG-UHFFFAOYSA-N 1-phenylhexan-1-one Chemical compound CCCCCC(=O)C1=CC=CC=C1 MAHPVQDVMLWUAG-UHFFFAOYSA-N 0.000 description 1
ACDMECIMTJZSCW-UHFFFAOYSA-N 1-tert-butyl-2-prop-2-enoxybenzene Chemical compound CC(C)(C)C1=CC=CC=C1OCC=C ACDMECIMTJZSCW-UHFFFAOYSA-N 0.000 description 1
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LMIREHQXDACYCS-UHFFFAOYSA-N CC(C)(C)C1=CC(Br)=CC(Br)=C1O.Br.Br Chemical compound CC(C)(C)C1=CC(Br)=CC(Br)=C1O.Br.Br LMIREHQXDACYCS-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000004780 naphthols Chemical class 0.000 description 1
ASAWAIQNAGKJFT-UHFFFAOYSA-N pent-4-ynoyl chloride Chemical compound ClC(=O)CCC#C ASAWAIQNAGKJFT-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/87—Preparation of ketenes or dimeric ketenes
- C07C45/89—Preparation of ketenes or dimeric ketenes from carboxylic acids, their anhydrides, esters or halides
- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO88885591A 1987-12-18 1988-12-16 Fremgangsmaate for fremstilling av substituerte aromatiskeforbindelser. NO885591L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US13465587A	1987-12-18	1987-12-18

Publications (2)

Publication Number	Publication Date
NO885591D0 NO885591D0 (no)	1988-12-16
NO885591L true NO885591L (no)	1989-06-19

Family

ID=22464348

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO88885591A NO885591L (no)	1987-12-18	1988-12-16	Fremgangsmaate for fremstilling av substituerte aromatiskeforbindelser.

Country Status (10)

Country	Link
EP (1)	EP0321432A1 (fr)
JP (1)	JPH01279847A (fr)
KR (1)	KR890009834A (fr)
AU (1)	AU2699988A (fr)
DK (1)	DK701688A (fr)
FI (1)	FI885818A7 (fr)
IL (1)	IL88674A0 (fr)
NO (1)	NO885591L (fr)
PT (1)	PT89235A (fr)
ZA (1)	ZA889439B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4847303A (en) *	1987-11-23	1989-07-11	The Procter & Gamble Company	Tert-butylphenyl compounds useful as anti-inflammatory agents
US5126487A (en) *	1991-03-26	1992-06-30	The Procter & Gamble Company	Process for the preparation of 2-alkyl-4-acyl-6-tert-butylphenol compounds
US5674891A (en) *	1994-07-27	1997-10-07	The Procter & Gamble Company	Dihydrobenzothiophene compounds useful as anti-inflammatory agents
CN1191243C (zh) *	1994-07-27	2005-03-02	范德比尔特大学	用作抗炎剂的二氢苯并呋喃和相关化合物
US5684002A (en) *	1994-09-07	1997-11-04	The Procter & Gamble Company	Dihydorbenzofuran and related compounds useful as anti-inflammatory agents
US5672620A (en) *	1996-02-01	1997-09-30	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5684031A (en) *	1996-02-01	1997-11-04	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents

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US3985783A (en) *	1975-06-09	1976-10-12	The Dow Chemical Company	Process for ring acylation of phenols
US4130666A (en) *	1977-05-16	1978-12-19	Riker Laboratories, Inc.	Anti-inflammatory method
DE3323127C2 (de) *	1983-06-27	1987-01-22	Institut Chimii Akademii Nauk Estonskoj Ssr, Tallin	Phenylderivate von 2,4-Dimethyl-2-hexen und deren Verwendung
US4708966A (en) *	1986-06-27	1987-11-24	The Procter & Gamble Company	Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation

1988
- 1988-12-13 IL IL88674A patent/IL88674A0/xx unknown
- 1988-12-15 EP EP88870187A patent/EP0321432A1/fr not_active Withdrawn
- 1988-12-16 NO NO88885591A patent/NO885591L/no unknown
- 1988-12-16 AU AU26999/88A patent/AU2699988A/en not_active Abandoned
- 1988-12-16 FI FI885818A patent/FI885818A7/fi not_active Application Discontinuation
- 1988-12-16 PT PT89235A patent/PT89235A/pt not_active Application Discontinuation
- 1988-12-16 DK DK701688A patent/DK701688A/da not_active Application Discontinuation
- 1988-12-17 KR KR1019880016886A patent/KR890009834A/ko not_active Withdrawn
- 1988-12-19 ZA ZA889439A patent/ZA889439B/xx unknown
- 1988-12-19 JP JP63320320A patent/JPH01279847A/ja active Pending

Also Published As

Publication number	Publication date
NO885591D0 (no)	1988-12-16
ZA889439B (en)	1989-09-27
EP0321432A1 (fr)	1989-06-21
PT89235A (pt)	1989-12-29
AU2699988A (en)	1989-06-29
JPH01279847A (ja)	1989-11-10
IL88674A0 (en)	1989-07-31
FI885818A7 (fi)	1989-06-19
DK701688D0 (da)	1988-12-16
DK701688A (da)	1989-06-19
KR890009834A (ko)	1989-08-04
FI885818A0 (fi)	1988-12-16

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