JPS5912093B2 - シクロブタノンまたはシクロブテノンの製法 - Google Patents
シクロブタノンまたはシクロブテノンの製法Info
- Publication number
- JPS5912093B2 JPS5912093B2 JP50105692A JP10569275A JPS5912093B2 JP S5912093 B2 JPS5912093 B2 JP S5912093B2 JP 50105692 A JP50105692 A JP 50105692A JP 10569275 A JP10569275 A JP 10569275A JP S5912093 B2 JPS5912093 B2 JP S5912093B2
- Authority
- JP
- Japan
- Prior art keywords
- zinc
- dcac
- compound
- mmol
- mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 title claims description 15
- DFLRGCFWSRELEL-UHFFFAOYSA-N cyclobut-2-en-1-one Chemical compound O=C1CC=C1 DFLRGCFWSRELEL-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title description 17
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000011701 zinc Substances 0.000 claims description 44
- 229910052725 zinc Inorganic materials 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 18
- 150000002576 ketones Chemical class 0.000 claims description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 12
- 150000001983 dialkylethers Chemical class 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- -1 haloacetyl bromide Chemical compound 0.000 description 34
- 239000000203 mixture Substances 0.000 description 27
- 150000001923 cyclic compounds Chemical class 0.000 description 26
- 238000002474 experimental method Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 229940126062 Compound A Drugs 0.000 description 17
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 17
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WGZNOUWVAIGKDI-UHFFFAOYSA-N 2-chloroethenone Chemical compound ClC=C=O WGZNOUWVAIGKDI-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000006352 cycloaddition reaction Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- TVWWMKZMZALOFP-UHFFFAOYSA-N 2,2-dichloroethenone Chemical compound ClC(Cl)=C=O TVWWMKZMZALOFP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 235000010443 alginic acid Nutrition 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000005695 dehalogenation reaction Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 4
- 238000007157 ring contraction reaction Methods 0.000 description 4
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DZSNJASVIURWOG-UHFFFAOYSA-N 2,4-dimethylpenta-2,3-diene Chemical compound CC(C)=C=C(C)C DZSNJASVIURWOG-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- VPSIBBZAIGTOME-UHFFFAOYSA-N 3-methyl-1-propan-2-yloxybut-2-ene Chemical compound CC(C)OCC=C(C)C VPSIBBZAIGTOME-UHFFFAOYSA-N 0.000 description 2
- ZVASGJZYKNLXPW-UHFFFAOYSA-N 3-methylbut-2-enoxymethylbenzene Chemical compound CC(C)=CCOCC1=CC=CC=C1 ZVASGJZYKNLXPW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910001502 inorganic halide Inorganic materials 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical compound C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLOPRKKSAJMMEW-HTQZYQBOSA-N (-)-cis-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-HTQZYQBOSA-N 0.000 description 1
- VOVOITCISSQINJ-VXNVDRBHSA-N (2s,4s)-2-chloro-3,3-dimethyl-4-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=C[C@@H]1C(=O)[C@@H](Cl)C1(C)C VOVOITCISSQINJ-VXNVDRBHSA-N 0.000 description 1
- SHWRGPMBBKBLKB-FNORWQNLSA-N (3e)-pentadeca-1,3-diene Chemical group CCCCCCCCCCC\C=C\C=C SHWRGPMBBKBLKB-FNORWQNLSA-N 0.000 description 1
- ZOMAVUNDAPMWTK-YUMQZZPRSA-N (3r,4s)-4-chloro-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=C[C@H]1[C@H](Cl)C(=O)C1(C)C ZOMAVUNDAPMWTK-YUMQZZPRSA-N 0.000 description 1
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 1
- NDYRMWZHBBMBGD-HWKANZROSA-N (e)-1-ethoxybut-2-ene Chemical compound CCOC\C=C\C NDYRMWZHBBMBGD-HWKANZROSA-N 0.000 description 1
- VFCHHMABGOYOQI-SOFGYWHQSA-N (e)-2,4-dimethylhex-3-ene Chemical compound CC\C(C)=C\C(C)C VFCHHMABGOYOQI-SOFGYWHQSA-N 0.000 description 1
- FHHSSXNRVNXTBG-VOTSOKGWSA-N (e)-3-methylhex-3-ene Chemical compound CC\C=C(/C)CC FHHSSXNRVNXTBG-VOTSOKGWSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 1
- JIEJJGMNDWIGBJ-UHFFFAOYSA-N 1-propan-2-yloxypropane Chemical compound CCCOC(C)C JIEJJGMNDWIGBJ-UHFFFAOYSA-N 0.000 description 1
- VQCORKJNHWCDFL-UHFFFAOYSA-N 10-ethenylidenenonadecane Chemical compound CCCCCCCCCC(=C=C)CCCCCCCCC VQCORKJNHWCDFL-UHFFFAOYSA-N 0.000 description 1
- NVYASGXIJVBVPY-UHFFFAOYSA-N 2,2,2-trichloroacetyl bromide Chemical compound ClC(Cl)(Cl)C(Br)=O NVYASGXIJVBVPY-UHFFFAOYSA-N 0.000 description 1
- NJJLNWFTKZQEQB-UHFFFAOYSA-N 2,2,4,4-tetramethylcyclobutan-1-one Chemical compound CC1(C)CC(C)(C)C1=O NJJLNWFTKZQEQB-UHFFFAOYSA-N 0.000 description 1
- JCRWCWGNPPMDOT-UHFFFAOYSA-N 2,2-dichloroethenyl 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC=C(Cl)Cl JCRWCWGNPPMDOT-UHFFFAOYSA-N 0.000 description 1
- QJGFHDSKTKKTKN-UHFFFAOYSA-N 2,2-dimethyl-3-(phenylmethoxymethyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1COCC1=CC=CC=C1 QJGFHDSKTKKTKN-UHFFFAOYSA-N 0.000 description 1
- HUASXBAJMQJHCZ-UHFFFAOYSA-N 2,2-dimethyl-3-(propan-2-yloxymethyl)cyclopropane-1-carboxylic acid Chemical compound CC(C)OCC1C(C(O)=O)C1(C)C HUASXBAJMQJHCZ-UHFFFAOYSA-N 0.000 description 1
- WLRIGHMLOSYTOU-UHFFFAOYSA-N 2,2-dimethyl-3-propan-2-ylidenecyclopropane-1-carboxylic acid Chemical compound CC(C)=C1C(C(O)=O)C1(C)C WLRIGHMLOSYTOU-UHFFFAOYSA-N 0.000 description 1
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 description 1
- YFOKREQYTOOZCQ-UHFFFAOYSA-N 2,8-dimethylnona-4,5-diene Chemical compound CC(C)CC=C=CCC(C)C YFOKREQYTOOZCQ-UHFFFAOYSA-N 0.000 description 1
- VOVOITCISSQINJ-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=CC1C(=O)C(Cl)C1(C)C VOVOITCISSQINJ-UHFFFAOYSA-N 0.000 description 1
- XEGIYMUGTDAQFJ-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(phenylmethoxymethyl)cyclobutan-1-one Chemical compound CC1(C)C(Cl)C(=O)C1COCC1=CC=CC=C1 XEGIYMUGTDAQFJ-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- OXMWLXYKDKRADR-UHFFFAOYSA-N 3-ethyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CCC1C(C(O)=O)C1(C)C OXMWLXYKDKRADR-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical compound CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 description 1
- ZOMAVUNDAPMWTK-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=CC1C(Cl)C(=O)C1(C)C ZOMAVUNDAPMWTK-UHFFFAOYSA-N 0.000 description 1
- XAPUHLONFQTWSY-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-3-(phenylmethoxymethyl)cyclobutan-1-one Chemical compound C(C1=CC=CC=C1)OCC1C(C(C1(C)C)=O)Cl XAPUHLONFQTWSY-UHFFFAOYSA-N 0.000 description 1
- TWKNAOLSKWSFIZ-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-3-(propan-2-yloxymethyl)cyclobutan-1-one Chemical compound ClC1C(C(C1COC(C)C)(C)C)=O TWKNAOLSKWSFIZ-UHFFFAOYSA-N 0.000 description 1
- NEYLAVKYYZDLIN-UHFFFAOYSA-N 5-methylhexa-1,2-diene Chemical compound CC(C)CC=C=C NEYLAVKYYZDLIN-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003671 mercuric iodide Drugs 0.000 description 1
- YFDLHELOZYVNJE-UHFFFAOYSA-L mercury diiodide Chemical compound I[Hg]I YFDLHELOZYVNJE-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- QIRVGKYPAOQVNP-UHFFFAOYSA-N methylidenecyclobutane Chemical compound C=C1CCC1 QIRVGKYPAOQVNP-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- PODAMDNJNMAKAZ-UHFFFAOYSA-N penta-2,3-diene Chemical compound CC=C=CC PODAMDNJNMAKAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/517—Saturated compounds containing a keto group being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3864474 | 1974-09-04 | ||
| GB3864474A GB1524682A (en) | 1974-09-04 | 1974-09-04 | Process for the preparation of cyclobutanones |
| GB2181475 | 1975-05-21 | ||
| GB2181475 | 1975-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5170752A JPS5170752A (en) | 1976-06-18 |
| JPS5912093B2 true JPS5912093B2 (ja) | 1984-03-21 |
Family
ID=26255536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50105692A Expired JPS5912093B2 (ja) | 1974-09-04 | 1975-09-02 | シクロブタノンまたはシクロブテノンの製法 |
Country Status (10)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638356A1 (de) * | 1976-08-26 | 1978-03-02 | Bayer Ag | Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeureester |
| FI780931A7 (fi) * | 1977-03-31 | 1978-10-01 | Ciba Geigy | 2-(2'2'-dihalogenvinyl)-och 2-(2'2'2'-trihalogenetyl)-cyklobutanoner foerfarande foer deras framstaellning och deras anvaendning |
| DE2813337A1 (de) * | 1977-03-31 | 1978-10-05 | Ciba Geigy Ag | Verfahren zur herstellung von 2-(2', 2',2'-trihalogenaethyl)-4-halogencyclobutan1-onen |
| EP0002207B1 (de) * | 1977-11-24 | 1981-09-02 | Ciba-Geigy Ag | Dichlorvinylcyclobutanone, Verfahren zu deren Herstellung und ihre Verwendung als Zwischenprodukte für die Herstellung von Schädlingsbekämpfungsmitteln |
| FR2438022A2 (fr) * | 1978-10-02 | 1980-04-30 | Ciba Geigy Ag | Procede de preparation de cyclobutanones halogenees |
| JPS5553234A (en) * | 1978-10-11 | 1980-04-18 | Ciba Geigy Ag | 22*2**2**2**tribromoethyl**44chlorocyclobutanee 11one*its manufacture and intermediate for manufacture |
| JPS5692830A (en) * | 1979-12-07 | 1981-07-27 | Ciba Geigy Ag | 22*2**2**dichloroo3**3**3**trifluoropropyl** and 22*2**2**3**trichloroo3**3** difluoropropyl**44chlorocyclobutanee11one and their manufacture |
| DE3042218A1 (de) * | 1980-11-08 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | 2,2-dimethylcyclobutanone, und verfahren zu ihrer herstellung |
| US5420356A (en) * | 1993-08-11 | 1995-05-30 | Sumitomo Chemical Company, Limited | Process for producing cyclobutanones |
| ES2951876T3 (es) | 2019-07-17 | 2023-10-25 | Shinetsu Chemical Co | Compuesto diéster que tiene un anillo de dimetilciclobutano, un procedimiento para preparar el mismo, y un procedimiento para preparar compuesto de dimetilciclobutano derivado del compuesto diéster |
| ES2955782T3 (es) | 2019-07-17 | 2023-12-07 | Shinetsu Chemical Co | Compuestos de dimetilciclobutanona, compuestos de dimetilciclobutano y procesos para preparar los mismos |
-
1975
- 1975-08-29 HU HU75SE1794A patent/HU176610B/hu unknown
- 1975-09-02 CH CH1133775A patent/CH617653A5/de not_active IP Right Cessation
- 1975-09-02 DE DE19752539048 patent/DE2539048A1/de active Granted
- 1975-09-02 DD DD188142A patent/DD124724A5/xx unknown
- 1975-09-02 JP JP50105692A patent/JPS5912093B2/ja not_active Expired
- 1975-09-02 FR FR7526844A patent/FR2299302A1/fr active Granted
- 1975-09-02 BR BR7505619*A patent/BR7505619A/pt unknown
- 1975-09-02 IL IL48032A patent/IL48032A/xx unknown
- 1975-09-02 IT IT26821/75A patent/IT1042237B/it active
- 1975-09-03 NL NLAANVRAGE7510373,A patent/NL186314C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2299302A1 (fr) | 1976-08-27 |
| IL48032A (en) | 1979-10-31 |
| DE2539048A1 (de) | 1976-03-25 |
| IL48032A0 (en) | 1975-11-25 |
| BR7505619A (pt) | 1976-08-03 |
| CH617653A5 (en) | 1980-06-13 |
| DE2539048C2 (enrdf_load_stackoverflow) | 1988-03-31 |
| NL7510373A (nl) | 1976-03-08 |
| JPS5170752A (en) | 1976-06-18 |
| IT1042237B (it) | 1980-01-30 |
| NL186314C (nl) | 1990-11-01 |
| HU176610B (en) | 1981-03-28 |
| AU8446475A (en) | 1977-03-10 |
| DD124724A5 (enrdf_load_stackoverflow) | 1977-03-09 |
| FR2299302B1 (enrdf_load_stackoverflow) | 1978-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4723033A (en) | Manufacture of optically active α-arylalkanoic acids and precursors thereof | |
| JPS5912093B2 (ja) | シクロブタノンまたはシクロブテノンの製法 | |
| US5380920A (en) | Preparation of R/S-γ-lipoic acid or R/S-α-lipoic acid | |
| SU722479A3 (ru) | Способ рацемизации оптически активных галогенангидридов 2,2-диметил-3 /1-алкенил/-циклопропан-1-карбоновых кислот | |
| US4028418A (en) | Process for the preparation of cyclobutanones | |
| Bachman et al. | Diethyl methylenemalonate | |
| US4234739A (en) | Method for preparing glyoxylic acids and derivatives thereof | |
| US2466420A (en) | Ketene condensation products with aldehydes | |
| GB2123416A (en) | Preparing haloalkyl arylalkanoate esters and arylalkanoic acids | |
| JPS5835145A (ja) | α−アリ−ルアルカン酸エステルの製造法 | |
| US3652652A (en) | 3-methallyllevulinates and preparation thereof | |
| JPS6117820B2 (enrdf_load_stackoverflow) | ||
| Honda et al. | A novel synthetic method of optically pure α-substituted aldehyde acetals by the use of reductive 1, 2-rearrangement | |
| JPS6412261B2 (enrdf_load_stackoverflow) | ||
| Zook et al. | Addition of hydrogen bromide to trans-4-heptenoic acid | |
| JPS5850209B2 (ja) | ２ ２− ジメチル−３−（２ ２−ジハロビニル）−シクロプロパンカルボンサンユウドウタイノ セイゾウホウ | |
| JPH01113341A (ja) | カルボン酸メチルエステルの製造法 | |
| JPS5929058B2 (ja) | 菊酸エステルの新規な製造法 | |
| JPS6020372B2 (ja) | 置換シクロプロパンカルボン酸エステルの製造方法 | |
| LUTZ et al. | THE CIS AND TRANS 3-AROYL-2, 3-DIMETHYLACRYLIC1 ACIDS WITH PARTICULAR REFERENCE TO THE OPEN-CHAIN AND CYCLIC FORMS OF THE CIS DERIVATIVES | |
| EP0110671B1 (en) | Preparation of optically active alpha-arylalkanoic acids and precursors thereof | |
| CA1164469A (en) | Preparing arylalkanoate esters via 1-haloalkyl aryl ketals and zinc carboxylate catalysts | |
| US3275683A (en) | Process for producing 2-phenylglutaric acid and derivatives thereof | |
| JP5074196B2 (ja) | シクロペンテノンの合成 | |
| US2075035A (en) | Process for preparing carboxylic anhydrides |