NO116122B - - Google Patents
Info
- Publication number
- NO116122B NO116122B NO15833865A NO15833865A NO116122B NO 116122 B NO116122 B NO 116122B NO 15833865 A NO15833865 A NO 15833865A NO 15833865 A NO15833865 A NO 15833865A NO 116122 B NO116122 B NO 116122B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- melting point
- alkyl
- carbon atoms
- yield
- Prior art date
Links
- -1 phenylalkyloxy Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- FPOQLQZHRCEVOT-UHFFFAOYSA-N N-hydroxy-2-phenylacetamide Chemical class ONC(=O)CC1=CC=CC=C1 FPOQLQZHRCEVOT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 239000003279 phenylacetic acid Substances 0.000 claims description 2
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000010186 staining Methods 0.000 description 15
- 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 12
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- YGUSJHXZIZCUKY-UHFFFAOYSA-N 2-(4-cyclopentyloxyphenyl)-N-hydroxyacetamide Chemical compound C1(CCCC1)OC1=CC=C(C=C1)CC(=O)NO YGUSJHXZIZCUKY-UHFFFAOYSA-N 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- JFPSDQKIDROJSD-UHFFFAOYSA-N 1-(4-butoxy-3-methylphenyl)ethanone Chemical compound CCCCOC1=CC=C(C(C)=O)C=C1C JFPSDQKIDROJSD-UHFFFAOYSA-N 0.000 description 2
- YYLCJWIQUFHYMY-UHFFFAOYSA-N 1-(4-butoxyphenyl)ethanone Chemical compound CCCCOC1=CC=C(C(C)=O)C=C1 YYLCJWIQUFHYMY-UHFFFAOYSA-N 0.000 description 2
- CMPGCNLVAWKWAO-UHFFFAOYSA-N 1-(4-cyclopentyloxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1CCCC1 CMPGCNLVAWKWAO-UHFFFAOYSA-N 0.000 description 2
- WKAZTGOEVXZSBE-UHFFFAOYSA-N 1-[4-(2-phenylethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCC1=CC=CC=C1 WKAZTGOEVXZSBE-UHFFFAOYSA-N 0.000 description 2
- APYAPSPMAOAUDX-UHFFFAOYSA-N 2-(4-butoxy-3-methylphenyl)-n-hydroxyacetamide Chemical compound CCCCOC1=CC=C(CC(=O)NO)C=C1C APYAPSPMAOAUDX-UHFFFAOYSA-N 0.000 description 2
- BRBTWQMWSVOGOW-UHFFFAOYSA-N 2-(4-butoxy-3-methylphenyl)acetic acid Chemical compound CCCCOC1=CC=C(CC(O)=O)C=C1C BRBTWQMWSVOGOW-UHFFFAOYSA-N 0.000 description 2
- KLJMYYFCWBVKEE-UHFFFAOYSA-N 2-(4-butoxyphenyl)acetic acid Chemical compound CCCCOC1=CC=C(CC(O)=O)C=C1 KLJMYYFCWBVKEE-UHFFFAOYSA-N 0.000 description 2
- JYNKBQIDIFHNCY-UHFFFAOYSA-N 2-(4-cyclopentyloxyphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC1CCCC1 JYNKBQIDIFHNCY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- FXJXPXZFUVLJBL-UHFFFAOYSA-N N-hydroxy-2-[3-methyl-4-(2-methylpropoxy)phenyl]acetamide Chemical compound C(C(C)C)OC1=C(C=C(C=C1)CC(=O)NO)C FXJXPXZFUVLJBL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- MXJWRABVEGLYDG-UHFFFAOYSA-N bufexamac Chemical compound CCCCOC1=CC=C(CC(=O)NO)C=C1 MXJWRABVEGLYDG-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- AAQWPEAOGARMIU-UHFFFAOYSA-N ethyl 2-(4-butoxy-3-methylphenyl)acetate Chemical compound C(CCC)OC1=C(C=C(C=C1)CC(=O)OCC)C AAQWPEAOGARMIU-UHFFFAOYSA-N 0.000 description 2
- PUIBRHJUTVHVPI-UHFFFAOYSA-N ethyl 2-(4-butoxyphenyl)acetate Chemical compound CCCCOC1=CC=C(CC(=O)OCC)C=C1 PUIBRHJUTVHVPI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- LJMBSDMRFKFQDW-UHFFFAOYSA-N n-hydroxy-2-[4-(2-phenylethoxy)phenyl]acetamide Chemical compound C1=CC(CC(=O)NO)=CC=C1OCCC1=CC=CC=C1 LJMBSDMRFKFQDW-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- WAXIFMGAKWIFDQ-UHFFFAOYSA-N 1-tert-butyl-4-(chloromethyl)benzene Chemical compound CC(C)(C)C1=CC=C(CCl)C=C1 WAXIFMGAKWIFDQ-UHFFFAOYSA-N 0.000 description 1
- MICUQIINHNFYMW-UHFFFAOYSA-N 2-(4-butylphenyl)-n-hydroxyacetamide Chemical compound CCCCC1=CC=C(CC(=O)NO)C=C1 MICUQIINHNFYMW-UHFFFAOYSA-N 0.000 description 1
- TXCTURVQEPLVTE-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-n-hydroxyacetamide Chemical compound CC(C)(C)C1=CC=C(CC(=O)NO)C=C1 TXCTURVQEPLVTE-UHFFFAOYSA-N 0.000 description 1
- QKJPXROEIJPNHG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC=C(CC#N)C=C1 QKJPXROEIJPNHG-UHFFFAOYSA-N 0.000 description 1
- FWNJTUVHYUSEDP-UHFFFAOYSA-N 2-[4-(2-cyclohexylethoxy)phenyl]-n-hydroxyacetamide Chemical compound C1=CC(CC(=O)NO)=CC=C1OCCC1CCCCC1 FWNJTUVHYUSEDP-UHFFFAOYSA-N 0.000 description 1
- SUFVSGPQUUMMDC-UHFFFAOYSA-N 2-[4-(2-phenylethoxy)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCCC1=CC=CC=C1 SUFVSGPQUUMMDC-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KJTLHVIFQSMSCX-UHFFFAOYSA-N C(CCCCC)OC1=CC=C(C=C1)CC(=O)NO Chemical compound C(CCCCC)OC1=CC=C(C=C1)CC(=O)NO KJTLHVIFQSMSCX-UHFFFAOYSA-N 0.000 description 1
- FXKIPLFZIMGPDQ-UHFFFAOYSA-N N-hydroxy-2-(4-octoxyphenyl)acetamide Chemical compound C(CCCCCCC)OC1=CC=C(C=C1)CC(=O)NO FXKIPLFZIMGPDQ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- WVMMIDGLSNLLEN-UHFFFAOYSA-N ethyl 2-(4-cyclopentyloxyphenyl)acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OC1CCCC1 WVMMIDGLSNLLEN-UHFFFAOYSA-N 0.000 description 1
- UBOXUSURHVGIJN-UHFFFAOYSA-N ethyl 2-[3-methyl-4-(2-methylpropoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC(C)=C(OCC(C)C)C=C1 UBOXUSURHVGIJN-UHFFFAOYSA-N 0.000 description 1
- TVMFBTMPYCWLPU-UHFFFAOYSA-N ethyl 2-[4-(2-phenylethoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OCCC2=CC=CC=C2)C=C1 TVMFBTMPYCWLPU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- HXVTYMWVMVKVTF-UHFFFAOYSA-N methyl 2-(4-tert-butylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(C(C)(C)C)C=C1 HXVTYMWVMVKVTF-UHFFFAOYSA-N 0.000 description 1
- LDCVQEHNEIJAPV-UHFFFAOYSA-N n-hydroxy-2-(4-propoxyphenyl)acetamide Chemical compound CCCOC1=CC=C(CC(=O)NO)C=C1 LDCVQEHNEIJAPV-UHFFFAOYSA-N 0.000 description 1
- OIWYKTQRGOGUJE-UHFFFAOYSA-N n-hydroxy-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound CC(C)COC1=CC=C(CC(=O)NO)C=C1 OIWYKTQRGOGUJE-UHFFFAOYSA-N 0.000 description 1
- KXWBJMRKTBNVNY-UHFFFAOYSA-N n-hydroxy-2-[4-(2-methylpropyl)phenyl]acetamide Chemical compound CC(C)CC1=CC=C(CC(=O)NO)C=C1 KXWBJMRKTBNVNY-UHFFFAOYSA-N 0.000 description 1
- WKBQEFJEBCWCPM-UHFFFAOYSA-N n-hydroxy-2-[4-(3-methylbutoxy)phenyl]acetamide Chemical compound CC(C)CCOC1=CC=C(CC(=O)NO)C=C1 WKBQEFJEBCWCPM-UHFFFAOYSA-N 0.000 description 1
- RKWMMVXJQIRTPT-UHFFFAOYSA-N n-hydroxy-2-[4-(3-phenylpropoxy)phenyl]acetamide Chemical compound C1=CC(CC(=O)NO)=CC=C1OCCCC1=CC=CC=C1 RKWMMVXJQIRTPT-UHFFFAOYSA-N 0.000 description 1
- XYRBAZYYMCJCBY-UHFFFAOYSA-N n-hydroxy-2-phenylpentanamide Chemical compound CCCC(C(=O)NO)C1=CC=CC=C1 XYRBAZYYMCJCBY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C45/68—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 increase in the number of carbon atoms
- C07C45/70—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE521207 | 1964-06-05 | ||
| BE10327 | 1965-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116122B true NO116122B (fr) | 1969-02-03 |
Family
ID=25646993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15833865A NO116122B (fr) | 1964-06-05 | 1965-06-02 |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH446379A (fr) |
| NO (1) | NO116122B (fr) |
-
1965
- 1965-06-02 NO NO15833865A patent/NO116122B/no unknown
- 1965-06-04 CH CH784865A patent/CH446379A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH446379A (fr) | 1967-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO158338B (no) | Anordning til drift av en gripekran for en lastebro til lasting eller lossing av et skip. | |
| WO2019179265A1 (fr) | Procédé de préparation d'un herbicide à base d'acide phénoxycarboxylique | |
| Truce et al. | The Stereochemistry of the Base-catalyzed Addition of p-Toluenethiol to Sodium and Ethyl Phenylpropiolate1, 2 | |
| McBee et al. | Nucleophilic Displacement Reactions of Polyhalogenated Cyclopentadienes and Cyclopentenes. I | |
| WO2019179267A1 (fr) | Procédé de préparation d'herbicides à base d'acide phénoxycarboxylique | |
| Newman et al. | Synthesis of a series of substituted phenylpropiolic acids | |
| Galat | The Preparation of 2, 4, 5-Trichlorophenoxyacetic Acid (2, 4, 5-T) | |
| Blicke et al. | 5-Ethyl-5-(α-thienyl)-barbituric Acid | |
| DK174496B1 (da) | Fremgangsmåde til fremstilling af 5-(2,5-dimethylphenoxy)-2,2-dimethylpentansyre | |
| RAUH et al. | The synthesis of 1, 2-cyclohexanedionedioxime (nioxime) | |
| NO116122B (fr) | ||
| SU799647A3 (ru) | Способ получени производныхиНдАНА | |
| US3980699A (en) | 2-Naphthyl acetic acid derivatives | |
| Erickson et al. | The Base-Catalyzed Conversion of Ketenes and Ketene Dimers to Ketene Trimers | |
| NO128222B (fr) | ||
| US3803245A (en) | Process for preparing 2-(6-methoxy-2-naphthyl)propionic acid,and intermediate therefor | |
| Buggle et al. | Ring-expansion of 3-arylinden-1-ones with lithium methylsulphinylmethanide | |
| Jacobson | Insect sex attractants. III. The optical resolution of DL-10-acetoxy-cis-7-hexadecen-1-ol | |
| Mowry et al. | Vinyl Aromatic Compounds. V. Ortho-, Meta-and Para-Isopropenylbiphenyls1 | |
| US4016197A (en) | 4-Acetamidophenyl-p-isobutyl hydratropate | |
| Koelsch et al. | THE PREPARATION OF SOME CHLOROMETHYLINDENES AND THE DETERMINATION OF THEIR REACTIVITIES TOWARDS SODIUM IODIDE1 | |
| Cartwright et al. | 670. The synthesis of γ-resorcylic acid (2: 6-dihydroxybenzoic acid) | |
| Kipnis et al. | New Compounds. Syntheses from Acetoheterocycles | |
| Bachmann et al. | Synthesis of 1-Keto-Δ4a, 10a-dodecahydrophenanthrene, cis-9-Methyl-1-decalone, and other Cyclic Ketones | |
| Schiessler et al. | Oxidation of a methylene group with hypochlorite |