GB806710A - Reactions of organomagnesium chloride complexes - Google Patents
Reactions of organomagnesium chloride complexesInfo
- Publication number
- GB806710A GB806710A GB13712/56A GB1371256A GB806710A GB 806710 A GB806710 A GB 806710A GB 13712/56 A GB13712/56 A GB 13712/56A GB 1371256 A GB1371256 A GB 1371256A GB 806710 A GB806710 A GB 806710A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- gives
- carbinol
- divinyl
- ethyl
- 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
- -1 organomagnesium chloride complexes Chemical class 0.000 title abstract 25
- 238000006243 chemical reaction Methods 0.000 title abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 12
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 abstract 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- 150000002825 nitriles Chemical class 0.000 abstract 5
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 4
- 229920002554 vinyl polymer Polymers 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 abstract 3
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 230000018044 dehydration Effects 0.000 abstract 3
- 238000006297 dehydration reaction Methods 0.000 abstract 3
- 229960002097 dibutylsuccinate Drugs 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 3
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical group ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 abstract 2
- LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 abstract 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- NDKYEUQMPZIGFN-UHFFFAOYSA-N Butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 abstract 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 abstract 2
- 229940040102 levulinic acid Drugs 0.000 abstract 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 2
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 abstract 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- MKDDYCLBFBDYRQ-UHFFFAOYSA-N (4-ethoxyphenyl) acetate Chemical group CCOC1=CC=C(OC(C)=O)C=C1 MKDDYCLBFBDYRQ-UHFFFAOYSA-N 0.000 abstract 1
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 abstract 1
- BLTWAWYHQFQXPV-UHFFFAOYSA-N 1,1,4,4-tetrakis(3,4-dichlorophenyl)butane-1,4-diol Chemical compound OC(CCC(O)(C1=CC(Cl)=C(Cl)C=C1)C1=CC(Cl)=C(Cl)C=C1)(C1=CC(Cl)=C(Cl)C=C1)C1=CC(Cl)=C(Cl)C=C1 BLTWAWYHQFQXPV-UHFFFAOYSA-N 0.000 abstract 1
- JMRZFJDGTUEABN-UHFFFAOYSA-N 1,1,4,4-tetrakis(4-chlorophenyl)butane-1,4-diol Chemical compound OC(CCC(O)(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1)(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1 JMRZFJDGTUEABN-UHFFFAOYSA-N 0.000 abstract 1
- AYCFYSUYIXPJRU-UHFFFAOYSA-N 1,1,4-triphenylpentane-1,4-diol Chemical compound C1(=CC=CC=C1)C(CCC(C)(O)C1=CC=CC=C1)(O)C1=CC=CC=C1 AYCFYSUYIXPJRU-UHFFFAOYSA-N 0.000 abstract 1
- STUJYKJUDMZHHU-UHFFFAOYSA-N 1,1,4-tris(4-ethoxyphenyl)pentane-1,4-diol Chemical compound C1(=CC=C(C=C1)OCC)C(CCC(C)(O)C1=CC=C(C=C1)OCC)(O)C1=CC=C(C=C1)OCC STUJYKJUDMZHHU-UHFFFAOYSA-N 0.000 abstract 1
- YKLSTQWKQDQOPB-UHFFFAOYSA-N 1,1-bis(2-phenylphenyl)dodecan-1-ol Chemical compound C1(=C(C=CC=C1)C(CCCCCCCCCCC)(O)C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 YKLSTQWKQDQOPB-UHFFFAOYSA-N 0.000 abstract 1
- SKEXLXIWNGRUOT-UHFFFAOYSA-N 1,1-bis(3,4-dichlorophenyl)ethanol Chemical compound CC(O)(C1=CC(Cl)=C(Cl)C=C1)C1=CC(Cl)=C(Cl)C=C1 SKEXLXIWNGRUOT-UHFFFAOYSA-N 0.000 abstract 1
- FGWWCGVPYRHTGX-UHFFFAOYSA-N 1,1-bis(4-ethoxyphenyl)ethanol Chemical compound C1(=CC=C(C=C1)OCC)C(O)(C)C1=CC=C(C=C1)OCC FGWWCGVPYRHTGX-UHFFFAOYSA-N 0.000 abstract 1
- CHALCBAZQAGHSU-UHFFFAOYSA-N 1,4-diphenylpenta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 CHALCBAZQAGHSU-UHFFFAOYSA-N 0.000 abstract 1
- XLCJPQYALLFIPW-UHFFFAOYSA-N 1-(4-chlorophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(Cl)C=C1 XLCJPQYALLFIPW-UHFFFAOYSA-N 0.000 abstract 1
- ZVHLNFHDJUQTGG-UHFFFAOYSA-N 1-[1,4-bis(4-ethoxyphenyl)penta-1,3-dienyl]-4-ethoxybenzene Chemical compound C1(=CC=C(C=C1)OCC)C(=CC=C(C)C1=CC=C(C=C1)OCC)C1=CC=C(C=C1)OCC ZVHLNFHDJUQTGG-UHFFFAOYSA-N 0.000 abstract 1
- YRGAYAGBVIXNAQ-UHFFFAOYSA-N 1-chloro-4-methoxybenzene Chemical group COC1=CC=C(Cl)C=C1 YRGAYAGBVIXNAQ-UHFFFAOYSA-N 0.000 abstract 1
- OABJHHHKRJCLDL-UHFFFAOYSA-N 10-ethenyldodeca-9,11-dienoic acid Chemical compound C=CC(=CCCCCCCCC(=O)O)C=C OABJHHHKRJCLDL-UHFFFAOYSA-N 0.000 abstract 1
- QOJQBWSZHCKOLL-UHFFFAOYSA-N 2,6-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C)=C1C=O QOJQBWSZHCKOLL-UHFFFAOYSA-N 0.000 abstract 1
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ILWNKEDIOWMWDJ-UHFFFAOYSA-N 2-chloro-4-hydroxy-2-(2-phenylphenyl)pentanoic acid Chemical compound CC(CC(C1=CC=CC=C1C2=CC=CC=C2)(C(=O)O)Cl)O ILWNKEDIOWMWDJ-UHFFFAOYSA-N 0.000 abstract 1
- QDAZIEAOLNUKKZ-UHFFFAOYSA-N 2-ethenylbutanedinitrile Chemical compound C(=C)C(C#N)CC#N QDAZIEAOLNUKKZ-UHFFFAOYSA-N 0.000 abstract 1
- RMTPGIZYKKXIKB-UHFFFAOYSA-N 2-oxobut-3-enoyl chloride Chemical compound ClC(=O)C(=O)C=C RMTPGIZYKKXIKB-UHFFFAOYSA-N 0.000 abstract 1
- OBGULEFETWWHOC-UHFFFAOYSA-N 3,12-bis(ethenyl)tetradeca-1,13-diene-3,12-diol Chemical compound C(=C)C(C=C)(CCCCCCCCC(C=C)(O)C=C)O OBGULEFETWWHOC-UHFFFAOYSA-N 0.000 abstract 1
- ROPGCYCINPHUSM-UHFFFAOYSA-N 3,12-bis(ethenyl)tetradeca-1,3,11,13-tetraene Chemical compound C(=C)C(C=C)=CCCCCCCC=C(C=C)C=C ROPGCYCINPHUSM-UHFFFAOYSA-N 0.000 abstract 1
- JZUZRGLPUMLHKR-UHFFFAOYSA-N 3,6-bis(ethenyl)octa-1,3,5,7-tetraene Chemical compound C(=C)C(C=C)=CC=C(C=C)C=C JZUZRGLPUMLHKR-UHFFFAOYSA-N 0.000 abstract 1
- YYJDICOBLDNQEQ-UHFFFAOYSA-N 3,6-bis(ethenyl)octa-1,7-diene-3,6-diol Chemical compound C(=C)C(C=C)(CCC(C=C)(O)C=C)O YYJDICOBLDNQEQ-UHFFFAOYSA-N 0.000 abstract 1
- DAPYJCJWJLKSLD-UHFFFAOYSA-N 3-(4-methoxyphenyl)penta-1,4-dien-3-ol Chemical compound C(=C)C(O)(C1=CC=C(C=C1)OC)C=C DAPYJCJWJLKSLD-UHFFFAOYSA-N 0.000 abstract 1
- CGGSVHIYIBZVAQ-UHFFFAOYSA-N 3-[(2,4-dichlorophenoxy)methyl]penta-1,4-dien-3-ol Chemical compound C(=C)C(O)(COC1=C(C=C(C=C1)Cl)Cl)C=C CGGSVHIYIBZVAQ-UHFFFAOYSA-N 0.000 abstract 1
- PWRZOQJIHBFPJQ-UHFFFAOYSA-N 3-[2-(3-hydroxypenta-1,4-dien-3-yl)phenyl]penta-1,4-dien-3-ol Chemical compound C1(=C(C=CC=C1)C(O)(C=C)C=C)C(O)(C=C)C=C PWRZOQJIHBFPJQ-UHFFFAOYSA-N 0.000 abstract 1
- VNYREHWZYLLWAR-UHFFFAOYSA-N 3-[4-(3-hydroxypenta-1,4-dien-3-yl)phenyl]penta-1,4-dien-3-ol Chemical compound C1(=CC=C(C=C1)C(O)(C=C)C=C)C(O)(C=C)C=C VNYREHWZYLLWAR-UHFFFAOYSA-N 0.000 abstract 1
- SWUUSJPRVCPBLT-UHFFFAOYSA-N 3-ethenyltetradec-1-en-3-ol Chemical compound C(CCCCCCCCCC)C(C=C)(C=C)O SWUUSJPRVCPBLT-UHFFFAOYSA-N 0.000 abstract 1
- VXBVLYQDVVHAHZ-UHFFFAOYSA-N 3-methylidenepenta-1,4-diene Chemical compound C=CC(=C)C=C VXBVLYQDVVHAHZ-UHFFFAOYSA-N 0.000 abstract 1
- LNSCVZRMAHCQIH-UHFFFAOYSA-N 3-methylpenta-1,4-dien-3-ol Chemical compound C=CC(O)(C)C=C LNSCVZRMAHCQIH-UHFFFAOYSA-N 0.000 abstract 1
- DXRAVPORYZVGQZ-UHFFFAOYSA-N 3-pyridin-3-ylpenta-1,4-dien-3-ol Chemical compound C(=C)C(O)(C=1C=NC=CC1)C=C DXRAVPORYZVGQZ-UHFFFAOYSA-N 0.000 abstract 1
- PHUYGURFBULKPA-UHFFFAOYSA-N 4,4'-dichlorobenzhydrol Chemical compound C=1C=C(Cl)C=CC=1C(O)C1=CC=C(Cl)C=C1 PHUYGURFBULKPA-UHFFFAOYSA-N 0.000 abstract 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- HDJLSECJEQSPKW-UHFFFAOYSA-N Methyl 2-Furancarboxylate Chemical compound COC(=O)C1=CC=CO1 HDJLSECJEQSPKW-UHFFFAOYSA-N 0.000 abstract 1
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 108010021119 Trichosanthin Proteins 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229960004217 benzyl alcohol Drugs 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- UQMRAFJOBWOFNS-UHFFFAOYSA-N butyl 2-(2,4-dichlorophenoxy)acetate Chemical compound CCCCOC(=O)COC1=CC=C(Cl)C=C1Cl UQMRAFJOBWOFNS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 abstract 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 abstract 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 abstract 1
- BOSRTCDZXVRNHY-UHFFFAOYSA-N ethyl 10-ethenyl-10-hydroxydodec-11-enoate Chemical compound C(=C)C(CCCCCCCCC(OCC)=O)(O)C=C BOSRTCDZXVRNHY-UHFFFAOYSA-N 0.000 abstract 1
- VMHUTNDIFWWLGG-UHFFFAOYSA-N ethyl 2-ethenyl-2-hydroxybut-3-enoate Chemical compound OC(C(=O)OCC)(C=C)C=C VMHUTNDIFWWLGG-UHFFFAOYSA-N 0.000 abstract 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N ethyl butylhexanol Natural products CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical group CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical class F* 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 1
- MMPZYDUOPLQDHR-UHFFFAOYSA-N hexa-1,5-diene-3,4-dione Chemical compound C=CC(=O)C(=O)C=C MMPZYDUOPLQDHR-UHFFFAOYSA-N 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 abstract 1
- 229960001238 methylnicotinate Drugs 0.000 abstract 1
- 150000004002 naphthaldehydes Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000002829 nitrogen Chemical class 0.000 abstract 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- PAWKNQDIXPJKSO-UHFFFAOYSA-N octa-1,7-diene-3,6-diol Chemical compound C=CC(O)CCC(O)C=C PAWKNQDIXPJKSO-UHFFFAOYSA-N 0.000 abstract 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002734 organomagnesium group Chemical group 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- UIUWNILCHFBLEQ-UHFFFAOYSA-N pent-3-enoic acid Chemical compound CC=CCC(O)=O UIUWNILCHFBLEQ-UHFFFAOYSA-N 0.000 abstract 1
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003509 tertiary alcohols Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002348 vinylic group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A divinyldiketone ViCOCH2COVi (Vi=vinyl radical) polymerizes to form a resin having metal chelating properties.ALSO:Organo-magnesium chloride complexes of the formula R(MgCl)x.nQ, where R is an aryl, vinylic or heterocyclic group, x is 1 or 2, n from 1-3, and Q a heterocyclic ether having 5 or 6 atoms in the ring, of which only one is oxygen and the others carbon except that a substituted nitrogen may replace carbon in the 4-position of a 6-atom ring, the ring containing not more than one double bond and at least one carbon adjacent the oxygen being free of substituents, are reacted with a mono-ester, a polyester, an acyl halide, a nitrile, a cyanogen halide or an orthoester, and the products hydrolysed to give substituted alcohols, ketones, aldehydes, acetals, nitriles or esters. Where the reactant is an unsaturated ester or nitrile, e.g. an acrylic ester or nitrile, the product may be another ester or nitrile. The complexes are prepared as in Specifications 776,993, 777,158, 779,100 and 792,537, and the reactions effected as in Specification 802,517. Alcohol products may be dehydrated to mono- or poly-olefins. Thus where R is a chlorphenyl radical and the reactant a mono-ester, the product may be, e.g., <FORM:0806710/IV (b)/1> on dehydration. Similarly where R is heterocyclic the products may be <FORM:0806710/IV (b)/2> Among numerous examples wherein the compound Q is generally tetrahydrofuran but in a few cases is tetrahydropyran or its 2-methoxy or 2-ethoxy derivative, dihydropyran or tetrahydrofurfuryl ethyl ether, the following are typical: (1) R is vinyl and ethyl malonate yields 3,5 - divinyl - 3,5 - dihydroxypentadiene-1,6; (3) ethyl phthalate gives o-phenylene bis(divinyl carbinol); (4), (5) methyl formate gives acrolein or 1,4-pentadiene-3-ol; (7) butyl laurate gives 3-undecyl-1,4-pentadien-3-ol; (9), (10) diethyl oxalate yields ethyl 2-hydroxy-2-vinyl - 3 - butenoate or 3,4 - divinyl - 3,4 - divinyl - 3,4 - dihydroxy - 1,5 - hexadiene; (12) dibutyl succinate gives 3,6 - divinyl - 3,6 - dihydroxy - 1,7 - octadiene which is dehydrated by refluxing with acetic acid+iodine to 3,6-divinyl - 1,3,5,7 - octatetraene; (15), (16) diethyl sebacate yields ethyl 10,10-divinyl-10-hydroxycaprate, dehydrated to 10,10-divinyl-9-decenoate, or 3,12-divinyl-3,12-dihydroxy-1,13-tetradecadiene, dehydrated to 3,12-divinyl - 1,3,11,13 - tetradecatetraene; (18), (19) diethyl terephthalate gives ethyl p-(divinyl-hydroxymethyl) benzoate or p-phenylene bis(divinylcarbinol); (21) methyl anisate gives divinyl (p - methoxyphenyl) carbinol; (22) methyl furoate gives divinyl (a -furyl) carbinol; (23) methyl nicotinate gives divinyl (3-pyridyl) carbinol; (24) butyl 2,4-dichlorphenoxyacetate gives divinyl (2,4-dichlorphenoxymethyl) carbinol; (27) methyl acrylate gives methyl-4-pentenoate; (28), (29) acetyl chloride yields 3-methyl - 1,4 - pentadiene - 3 - ol, dehydrated to 2 - vinyl - 1,3 - butadiene, or methyl vinyl ketone; (35), (36) oxalyl chloride gives methylenepyruvyl chloride or diacrylyl; (37), (38) the acid chloride of monoethyl succinate gives ethyl b -acrylylpropionate or 3,6-dihydroxy-1,7-octadiene; (42), (43) a -furoyl chloride gives vinyl a -furyl ketone or divinyl (a -furyl) carbinol; (44) acetonitrile yields methyl vinyl ketone; (47) acrylonitrile gives b -vinyl propionitrile; (48), (49) fumaronitrile gives 2-vinyl succinonitrile or b -vinyl-b -acrylyl propionitrile; (50), (51) R is phenyl and methyl formate gives benzaldehyde or benzhydrol; (58) methyl levulinate gives 1,1,4-triphenyl-1,4-dihydroxypentane dehydrating to 1,1,4-triphenyl-1,3-pentadiene; (59) methyl acrylate gives methyl b -phenyl propionate; (66), (67) R is p-chlorophenyl and methyl formate yields p-chlorbenzaldehyde or di-(p-chlorphenyl) carbinol; (68) diethyl oxalate gives di-(p-chlorphenyl) hydroxyacetate; (69) dibutyl succinate yields 1,1,4,4 - tetra - (p - chlorphenyl) - 1,4 - dihydroxybutane; (72) oxalyl chloride gives di-p-chlorbenzoyl; (73) butyronitrile gives p-chlorphenyl propyl ketone; (74) R is o-tolyl, methyl formate giving o-tolualdehyde; (80) R is p-tolyl, and furoyl chloride gives p-tolyl a -furyl ketone; (81) R is anisyl, methyl formate giving anisaldehyde; (82) R is phenetyl and ethyl acetate gives di-(phenetyl) methyl carbinol; (84) methyl levulinate yields 1,1,4-tri-(phenetyl)-1,4-dihydroxypentane giving on dehydration 1,1,4-tri-(phenetyl)-1,3-pentadiene; (85) R is anisyl and furoyl chloride gives dianisyl (a -furyl) carbinol yielding 5,5-dianisyl levulinic acid on boiling with acid; (86) R is 3,4-dichlorphenyl, ethyl acetate giving di(3,4-dichlorphenyl) methyl carbinol; (88) dibutyl succinate gives 1,1,4,4-tetra-(3,4-dichlorphenyl)-1,4-dihydroxybutane dehydrated to the corresponding 1,3-butadiene; (98) the corresponding 1,2,4,5-tetrachlorphenyl compounds are formed when R is tetrachlorphenyl; (103) similarly where R is 2,3,4,5,6-pentachlorphenyl; (106) 2-m-xylyl magnesium chloride complex and methyl formate give 2,6-dimethylbenzaldehyde; (112) R is biphenylyl and butyl laurate gives 1,1-di-(biphenylyl)-1-dodecanol; (117) acrylonitrile gives b -biphenylylpropionitrile; (118), (119) R is tri- (or nona-) chlorbiphenylyl, methyl levulinate giving methyl 4-tri- (or nona-) chlorbiphenylyl - 4 - hydroxyvalerate giving the 3-pentenoate on dehydration; (120)-(122) R is naphthyl, reaction as in (4) or (29) yielding naphthaldehyde, dinaphthyl methyl carbinol or naphthyl methyl ketone; (125) R is trifluormethylphenyl (TFM), ethyl acetate giving di-(TFM) methyl carbinol which dehydrates to a ,a - di - (TFM) ethylene; (126)-(132) ethyl di-(TFM) hydroxyacetate, butyl 4,4-di-(TFM)-4 - hydroxybutyrate, 1,1,6,6 - tetra - (TFM) - 1,6 - dihydroxyhexane, di - (TFM) phenyl carbinol, di - (TFM) a - furyl carbinol giving on ring opening 5,5-di-(TFM) levulinic acid, methyl 4-(TFM)-4-hydroxyvalerate, and (TFM)-phenyl ketone are prepared as in earlier examples; (133)-(154) R is p-dimethyl (or ethyl) aminophenyl (DMA or DEA) and in analogous manner are prepared DMA-benzaldehyde, di-(DEA)-carbinol, di - (DMA) - 1 - dodecanol, ethyl di-(DEA) hydroxyacetate, tetra-(DMA) ethylene glycol, di-(DMA)-anisyl carbinol, di-(DMA)-(2,4 - dichlorphenoxymethyl) carbinol, DMA-methyl ketone, di-(p-dimethylaminobenzoyl) ethyl b - (p - dimethylaminobenzoyl) propionate, and like compounds; (165)-(174) R is chloranisyl and analogous reactions are effected; (175)-(184) R is chlorphenetyl; (185) R is ethyltetrachlorphenyl; (186)-(202) R is thienyl; (203)-(219) R is pyridyl; (220)-(236) R is furyl; (237)-(253) R is 5-chlor-2-thienyl; (254)-(265) R is mono-, di-, tri- or pentafluorphenyl; (266) R is 2-benzothiazolyl; (267) 2-benzoxazolyl; (268) 2-methyl-5-benzothiazolyl; (269)-(271) quinolyl; (272) 6-chlor-2-methoxy-9-acridyl; (273)-(275) various chlorpyrimidyl; (276)-(289) various cyclohexenyl, and (chlor) alkenyl; (290) 1,3-butadien-2-yl; (293) N-methyl pyrryl; (292)-(294) 4-vinylphenyl; (296), (297), (302) R is p-chlorphenyl and ethyl perfluorbutyrate (caprate or acetate) yields bis-p-chlorphenyl perfluorpropyl (nonyl or methyl) carbinol. Products containing unsaturated, e.g. vinyl, groups may be polymerized. Some have fungicidal properties. Some tertiary alcohols, especially the chlorine and fluorine derivatives, have insecticidal properties.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US806710XA | 1955-07-05 | 1955-07-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB806710A true GB806710A (en) | 1958-12-31 |
Family
ID=22158872
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13712/56A Expired GB806710A (en) | 1955-07-05 | 1956-06-01 | Reactions of organomagnesium chloride complexes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB806710A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2139215A (en) * | 1983-04-28 | 1984-11-07 | Roussel Uclaf | Production of thiophene acetic acid compounds |
-
1956
- 1956-06-01 GB GB13712/56A patent/GB806710A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2139215A (en) * | 1983-04-28 | 1984-11-07 | Roussel Uclaf | Production of thiophene acetic acid compounds |
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