CH491071A - Procédé de préparation de nouveaux acides dérivés du cyclopropane - Google Patents
Procédé de préparation de nouveaux acides dérivés du cyclopropaneInfo
- Publication number
- CH491071A CH491071A CH1143867A CH1143867A CH491071A CH 491071 A CH491071 A CH 491071A CH 1143867 A CH1143867 A CH 1143867A CH 1143867 A CH1143867 A CH 1143867A CH 491071 A CH491071 A CH 491071A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- radical
- trans
- methyl
- dimethyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 25
- 150000007513 acids Chemical class 0.000 title claims description 7
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 alkyl radical Chemical class 0.000 claims description 79
- 150000002148 esters Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- ATTZDURXGKNPIJ-UHFFFAOYSA-N 3-cyclopentylidene-1,2,2-trimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)C(C)(C)C1=C1CCCC1 ATTZDURXGKNPIJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000746 allylic group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- JMUJPNOTQMOTTC-UHFFFAOYSA-N 3-cyclobutylidene-1,2,2-trimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)C(C)(C)C1=C1CCC1 JMUJPNOTQMOTTC-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000008346 aqueous phase Substances 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 19
- 229910052753 mercury Inorganic materials 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000000605 extraction Methods 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XNDZQQSKSQTQQD-UHFFFAOYSA-N (+/-) 3-methyl-2-cyclohexen-1-ol Natural products CC1=CC(O)CCC1 XNDZQQSKSQTQQD-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
- KPKUYGKJBVWEPJ-UHFFFAOYSA-N 2,2,7-trimethylspiro[2.5]oct-7-ene-1-carboxylic acid Chemical class C1CCC(C)=CC21C(C)(C)C2C(O)=O KPKUYGKJBVWEPJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- NSDKPFYGZAAZGN-UHFFFAOYSA-N (3-methylcyclohex-2-en-1-yl)sulfonylbenzene Chemical compound C1CCC(C)=CC1S(=O)(=O)C1=CC=CC=C1 NSDKPFYGZAAZGN-UHFFFAOYSA-N 0.000 description 3
- PGDWJSMXNHAQDK-UHFFFAOYSA-N 1-bromo-3-ethylpent-2-ene Chemical compound CCC(CC)=CCBr PGDWJSMXNHAQDK-UHFFFAOYSA-N 0.000 description 3
- VKEDBRZQNMWREN-UHFFFAOYSA-N 2,2,7-trimethylspiro[2.5]oct-7-ene Chemical compound CC1(CC11C=C(CCC1)C)C VKEDBRZQNMWREN-UHFFFAOYSA-N 0.000 description 3
- LDVPUCRSDZQBRE-UHFFFAOYSA-N 2-cyclopentylideneethylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)CC=C1CCCC1 LDVPUCRSDZQBRE-UHFFFAOYSA-N 0.000 description 3
- WABDGHUESVCBGQ-UHFFFAOYSA-N 3-cyclohexylidene-1,2,2-trimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)C(C)(C)C1=C1CCCCC1 WABDGHUESVCBGQ-UHFFFAOYSA-N 0.000 description 3
- 235000019360 4-hexylresorcinol Nutrition 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CYVRTIAJWRWZAU-UHFFFAOYSA-N [3-(benzenesulfonyl)-1-phenylprop-1-enyl]benzene Chemical compound C=1C=CC=CC=1S(=O)(=O)CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 CYVRTIAJWRWZAU-UHFFFAOYSA-N 0.000 description 3
- ULOHIXCTQCANHN-UHFFFAOYSA-N [5-methyl-3-(2-methylpropyl)hex-2-enyl]sulfonylbenzene Chemical compound CC(C)CC(CC(C)C)=CCS(=O)(=O)C1=CC=CC=C1 ULOHIXCTQCANHN-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 229960002179 ephedrine Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- FOJILUGUSLGZEP-UHFFFAOYSA-N (3-bromo-1-phenylprop-1-enyl)benzene Chemical compound C=1C=CC=CC=1C(=CCBr)C1=CC=CC=C1 FOJILUGUSLGZEP-UHFFFAOYSA-N 0.000 description 2
- IAKCZIBGRMNCBF-UHFFFAOYSA-N 1,1-diphenylprop-2-en-1-ol Chemical compound C=1C=CC=CC=1C(C=C)(O)C1=CC=CC=C1 IAKCZIBGRMNCBF-UHFFFAOYSA-N 0.000 description 2
- XGKFCLKEGCJWSW-UHFFFAOYSA-N 1-ethenyl-4,4-dimethylcyclohexan-1-ol Chemical compound CC1(C)CCC(O)(C=C)CC1 XGKFCLKEGCJWSW-UHFFFAOYSA-N 0.000 description 2
- NENZDZJSFGHDNG-UHFFFAOYSA-N 1-ethenylcyclobutan-1-ol Chemical compound C=CC1(O)CCC1 NENZDZJSFGHDNG-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- WYXWUKXKMNEHKQ-UHFFFAOYSA-N 3-(2,2-diphenylethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 WYXWUKXKMNEHKQ-UHFFFAOYSA-N 0.000 description 2
- IITQJMYAYSNIMI-UHFFFAOYSA-N 3-Methyl-2-cyclohexen-1-one Chemical compound CC1=CC(=O)CCC1 IITQJMYAYSNIMI-UHFFFAOYSA-N 0.000 description 2
- YPVPQMCSLFDIKA-UHFFFAOYSA-N 3-ethylpent-1-ene Chemical compound CCC(CC)C=C YPVPQMCSLFDIKA-UHFFFAOYSA-N 0.000 description 2
- AVVWXEWXEQBSJO-UHFFFAOYSA-N 3-ethylpent-2-enylsulfonylbenzene Chemical compound CCC(CC)=CCS(=O)(=O)C1=CC=CC=C1 AVVWXEWXEQBSJO-UHFFFAOYSA-N 0.000 description 2
- QEJPOMAKYLPNKE-UHFFFAOYSA-N 4-(2-bromoethylidene)-2,6-dimethylheptane Chemical compound CC(C)CC(CC(C)C)=CCBr QEJPOMAKYLPNKE-UHFFFAOYSA-N 0.000 description 2
- ASRNVKGIZXLYBI-UHFFFAOYSA-N 4-ethenyl-2,6-dimethylheptan-4-ol Chemical compound CC(C)CC(O)(C=C)CC(C)C ASRNVKGIZXLYBI-UHFFFAOYSA-N 0.000 description 2
- QAEHGUGALZLTGP-UHFFFAOYSA-N 4-ethenylheptane Chemical compound CCCC(C=C)CCC QAEHGUGALZLTGP-UHFFFAOYSA-N 0.000 description 2
- SBQQUBMTHFCTBP-UHFFFAOYSA-N 4-ethenyloxan-4-ol Chemical compound C=CC1(O)CCOCC1 SBQQUBMTHFCTBP-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- INUPUCJZOICCKY-UHFFFAOYSA-N 4-methyl-3-propan-2-ylpent-1-en-3-ol Chemical compound CC(C)C(O)(C=C)C(C)C INUPUCJZOICCKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000010936 aqueous wash Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000001942 cyclopropanes Chemical class 0.000 description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UTXVCHVLDOLVPC-UHFFFAOYSA-N ethyl 3-methylbut-2-enoate Chemical compound CCOC(=O)C=C(C)C UTXVCHVLDOLVPC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- XEJITOJPSFRBPN-UHFFFAOYSA-N non-5-enoic acid Chemical compound CCCC=CCCCC(O)=O XEJITOJPSFRBPN-UHFFFAOYSA-N 0.000 description 2
- 238000006385 ozonation reaction Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- AULUDJRRNHDTJI-UHFFFAOYSA-N 1,1,3,3-tetramethylcyclohexane Chemical compound CC1(C)CCCC(C)(C)C1 AULUDJRRNHDTJI-UHFFFAOYSA-N 0.000 description 1
- OAQMBAJEEXIOAB-UHFFFAOYSA-N 1-bromo-4-methyl-3-propan-2-ylpent-2-ene Chemical compound CC(C)C(C(C)C)=CCBr OAQMBAJEEXIOAB-UHFFFAOYSA-N 0.000 description 1
- FHHAPOQQGSFCCN-UHFFFAOYSA-N 1-ethenyl-3,3,5,5-tetramethylcyclohexan-1-ol Chemical compound CC1(C)CC(C)(C)CC(O)(C=C)C1 FHHAPOQQGSFCCN-UHFFFAOYSA-N 0.000 description 1
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 description 1
- HYBPPJPMEYLNPQ-UHFFFAOYSA-N 2-(2-bromoethylidene)-1,3-dimethylcyclohexane Chemical compound CC1CCCC(C)C1=CCBr HYBPPJPMEYLNPQ-UHFFFAOYSA-N 0.000 description 1
- JHLHKCWPDVKWNS-UHFFFAOYSA-N 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(O)=O)=N1 JHLHKCWPDVKWNS-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- YLKLJBPHNWWPSF-ARJAWSKDSA-N 2-[(z)-but-2-enyl]-4-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound C\C=C/CC1=C(C)C(O)CC1=O YLKLJBPHNWWPSF-ARJAWSKDSA-N 0.000 description 1
- BBLAJMQEKRCPGP-UHFFFAOYSA-N 2-bromoethylidenecyclobutane Chemical compound BrCC=C1CCC1 BBLAJMQEKRCPGP-UHFFFAOYSA-N 0.000 description 1
- LUTZQLLTXUSAOF-UHFFFAOYSA-N 2-bromoethylidenecyclohexane Chemical compound BrCC=C1CCCCC1 LUTZQLLTXUSAOF-UHFFFAOYSA-N 0.000 description 1
- BQOYKRPKRYFJSK-UHFFFAOYSA-N 2-bromoethylidenecyclopentane Chemical compound BrCC=C1CCCC1 BQOYKRPKRYFJSK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ONTLTPFBSNQNHL-UHFFFAOYSA-N 2-cyclohexylideneethylsulfanylbenzene Chemical compound C(Sc1ccccc1)C=C1CCCCC1 ONTLTPFBSNQNHL-UHFFFAOYSA-N 0.000 description 1
- JLDKJTLDCPUTSM-UHFFFAOYSA-N 2-cyclohexylideneethylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)CC=C1CCCCC1 JLDKJTLDCPUTSM-UHFFFAOYSA-N 0.000 description 1
- MNQLVKDZYHGRNW-UHFFFAOYSA-N 2-diazoacetonitrile Chemical compound [N-]=[N+]=CC#N MNQLVKDZYHGRNW-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- JKRHDMUBVQVHRR-UHFFFAOYSA-N 2-methylpropan-2-ol;methylsulfinylmethane Chemical compound CS(C)=O.CC(C)(C)O JKRHDMUBVQVHRR-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 description 1
- VBNQMVZJHJDIKD-UHFFFAOYSA-N 3-(cyclopentylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C1CCCC1 VBNQMVZJHJDIKD-UHFFFAOYSA-N 0.000 description 1
- QUPRMGWZSNTJJX-UHFFFAOYSA-N 3-ethylpent-1-en-3-ol Chemical compound CCC(O)(CC)C=C QUPRMGWZSNTJJX-UHFFFAOYSA-N 0.000 description 1
- YIDJGNWPCMYDNC-UHFFFAOYSA-N 4-(2-bromoethylidene)-1,1-dimethylcyclohexane Chemical compound CC1(C)CCC(=CCBr)CC1 YIDJGNWPCMYDNC-UHFFFAOYSA-N 0.000 description 1
- DHONOAPSAYTYAY-UHFFFAOYSA-N 4-(2-bromoethylidene)heptane Chemical compound CCCC(CCC)=CCBr DHONOAPSAYTYAY-UHFFFAOYSA-N 0.000 description 1
- BMLGYCDPCPIHRF-UHFFFAOYSA-N 5-(2-bromoethylidene)-1,1,3,3-tetramethylcyclohexane Chemical compound CC1(C)CC(=CCBr)CC(C)(C)C1 BMLGYCDPCPIHRF-UHFFFAOYSA-N 0.000 description 1
- KMDYVCNYONBUHF-UHFFFAOYSA-N 5-ethenyl-1,1,3,3-tetramethylcyclohexane Chemical compound CC1(C)CC(C=C)CC(C)(C)C1 KMDYVCNYONBUHF-UHFFFAOYSA-N 0.000 description 1
- QREBEZZOILCJEP-UHFFFAOYSA-N 6-(3-methoxyphenyl)hex-1-en-3-one Chemical compound COC1=CC=CC(CCCC(=O)C=C)=C1 QREBEZZOILCJEP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- OEANTJPAWDMFLY-UHFFFAOYSA-N C1(CCCCC1)=COC(=O)C1CC1 Chemical compound C1(CCCCC1)=COC(=O)C1CC1 OEANTJPAWDMFLY-UHFFFAOYSA-N 0.000 description 1
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LDDOSDVZPSGLFZ-UHFFFAOYSA-N ethyl cyclopropanecarboxylate Chemical compound CCOC(=O)C1CC1 LDDOSDVZPSGLFZ-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/14—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing bromine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
- C07C35/045—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings containing a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/35—Unsaturated compounds having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mycology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR74405A FR1505423A (fr) | 1966-08-26 | 1966-08-26 | Nouveaux dérivés du cyclopropane et procédé de préparation |
| FR74404A FR1507192A (fr) | 1966-08-26 | 1966-08-26 | Nouvelles aryl allylsulfones et procédé de préparation |
| FR96425A FR1527844A (fr) | 1966-08-26 | 1967-02-24 | Nouveaux acides et esters dérivés du cyclopropane et procédé de préparation |
| FR110719A FR93112E (fr) | 1966-08-26 | 1967-06-16 | Nouveaux derivés du cyclopropane et procédé de préparation. |
| FR114833A FR94309E (fr) | 1966-08-26 | 1967-07-19 | Nouveaux dérivés du cyclopropane et procédé de préparation. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH491071A true CH491071A (fr) | 1970-05-31 |
Family
ID=38863090
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1143867A CH491071A (fr) | 1966-08-26 | 1967-08-15 | Procédé de préparation de nouveaux acides dérivés du cyclopropane |
| CH1843169A CH509961A (fr) | 1966-08-26 | 1967-08-15 | Procédé de préparation de nouveaux esters dérivés du cyclopropane |
| CH601569A CH491851A (fr) | 1966-08-26 | 1967-08-15 | Procédé de préparation de nouveaux acides dérivés du cyclopropane |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1843169A CH509961A (fr) | 1966-08-26 | 1967-08-15 | Procédé de préparation de nouveaux esters dérivés du cyclopropane |
| CH601569A CH491851A (fr) | 1966-08-26 | 1967-08-15 | Procédé de préparation de nouveaux acides dérivés du cyclopropane |
Country Status (14)
| Country | Link |
|---|---|
| AT (2) | AT287671B (cs) |
| BE (1) | BE702662A (cs) |
| CH (3) | CH491071A (cs) |
| CS (3) | CS180599B2 (cs) |
| DE (1) | DE1668603B2 (cs) |
| DK (3) | DK140720B (cs) |
| ES (3) | ES344436A1 (cs) |
| FR (5) | FR1505423A (cs) |
| GB (2) | GB1207371A (cs) |
| IL (2) | IL28541A (cs) |
| NL (2) | NL162060C (cs) |
| SE (2) | SE391330B (cs) |
| SU (1) | SU691076A3 (cs) |
| YU (5) | YU33952B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714153A (en) * | 1970-06-22 | 1973-01-30 | Roussel Uclaf | Novel cyclopropanecarboxylic acids |
| US4045469A (en) | 1971-06-25 | 1977-08-30 | The Procter & Gamble Company | Insecticidal esters of spiro carboxylic acids |
| BE791304A (fr) * | 1971-11-12 | 1973-05-14 | Procter & Gamble | Esters de 1-acenaphtenol |
| DE2326077C2 (de) * | 1972-05-25 | 1985-12-12 | National Research Development Corp., London | Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide |
| HU168432B (cs) * | 1973-08-15 | 1976-04-28 | ||
| DE2857020A1 (de) * | 1977-07-04 | 1981-01-08 | Astra Laekemedel Ab | A novel intermediate for preparation of therapeutically active pyridine compounds |
| DE2730515A1 (de) * | 1977-07-06 | 1979-01-18 | Bayer Ag | Substituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| FR2426673A1 (fr) * | 1978-05-25 | 1979-12-21 | Nat Res Dev | Pesticides du type pyrethrine |
| FR2428029A1 (fr) * | 1978-06-06 | 1980-01-04 | Roussel Uclaf | Esters d'acides cyclopropane carboxyliques substitues d'alcool a-cyane, leur procede de preparation et les compositions insecticides ou nematicides les renfermant |
| FR2443452A1 (fr) * | 1978-12-08 | 1980-07-04 | Roussel Uclaf | Nouveau procede de dedoublement de l'acide dl cis et dl trans chrysanthemique |
| FR2455024A1 (fr) * | 1979-04-03 | 1980-11-21 | Roussel Uclaf | Nouveau procede de dedoublement des acides d,l-cis 2,2-dimethyl 3-(2',2'-dihalovinyl) cyclopropane-1-carboxylique |
| FR2455018A1 (fr) * | 1979-04-26 | 1980-11-21 | Roussel Uclaf | Derives de l'allethrolone et leur procede de preparation |
| DE2926671A1 (de) * | 1979-07-02 | 1981-01-15 | Bayer Ag | Verfahren zur herstellung von cyclopropan-carbonsaeure-derivaten sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
| FR2479192A1 (fr) * | 1980-03-28 | 1981-10-02 | Roussel Uclaf | Procede de preparation de derives cyclopropaniques tetra-substitues |
| FR2490633A1 (fr) * | 1980-09-24 | 1982-03-26 | Roussel Uclaf | Procede de preparation de derives d'acides cyclopropane carboxyliques porteurs d'une fonction aldehyde |
| US5504245A (en) * | 1994-09-30 | 1996-04-02 | Eastman Chemical Company | Processes for the preparation of cyclopropanecarboxylic acid and derivatives thereof |
-
1966
- 1966-08-26 FR FR74405A patent/FR1505423A/fr not_active Expired
- 1966-08-26 FR FR74404A patent/FR1507192A/fr not_active Expired
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1967
- 1967-02-24 FR FR96425A patent/FR1527844A/fr not_active Expired
- 1967-06-16 FR FR110719A patent/FR93112E/fr not_active Expired
- 1967-07-19 FR FR114833A patent/FR94309E/fr not_active Expired
- 1967-08-14 BE BE702662D patent/BE702662A/xx not_active IP Right Cessation
- 1967-08-15 CH CH1143867A patent/CH491071A/fr not_active IP Right Cessation
- 1967-08-15 CH CH1843169A patent/CH509961A/fr not_active IP Right Cessation
- 1967-08-15 CH CH601569A patent/CH491851A/fr not_active IP Right Cessation
- 1967-08-22 IL IL2854167A patent/IL28541A/xx unknown
- 1967-08-22 IL IL3818267A patent/IL38182A/xx unknown
- 1967-08-23 CS CS565167A patent/CS180599B2/cs unknown
- 1967-08-23 CS CS602967A patent/CS180551B2/cs unknown
- 1967-08-23 CS CS565067A patent/CS180598B2/cs unknown
- 1967-08-25 SE SE13371A patent/SE391330B/xx unknown
- 1967-08-25 SE SE1192167A patent/SE369517B/xx unknown
- 1967-08-25 ES ES344436A patent/ES344436A1/es not_active Expired
- 1967-08-25 DE DE19671668603 patent/DE1668603B2/de active Granted
- 1967-08-25 DK DK430367A patent/DK140720B/da not_active IP Right Cessation
- 1967-08-25 ES ES344435A patent/ES344435A1/es not_active Expired
- 1967-08-26 YU YU168467A patent/YU33952B/xx unknown
- 1967-08-26 YU YU168567A patent/YU35568B/xx unknown
- 1967-08-26 SU SU671182999A patent/SU691076A3/ru active
- 1967-08-28 AT AT789967A patent/AT287671B/de active
- 1967-08-28 AT AT07278/69A patent/AT289754B/de not_active IP Right Cessation
- 1967-08-28 NL NL6711770A patent/NL162060C/xx not_active IP Right Cessation
- 1967-08-29 GB GB3954267A patent/GB1207371A/en not_active Expired
- 1967-08-29 GB GB836770A patent/GB1207372A/en not_active Expired
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1968
- 1968-02-23 YU YU42168A patent/YU33942B/xx unknown
- 1968-02-23 ES ES350839A patent/ES350839A1/es not_active Expired
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1970
- 1970-12-28 DK DK657370A patent/DK131538C/da not_active IP Right Cessation
- 1970-12-28 DK DK657270A patent/DK133579B/da unknown
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1978
- 1978-02-23 YU YU42178A patent/YU42168A/xx unknown
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1979
- 1979-08-30 NL NL7906529A patent/NL172853C/xx not_active IP Right Cessation
- 1979-11-27 YU YU290379A patent/YU290379A/xx unknown
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