JPS6123778B2 - - Google Patents
Info
- Publication number
- JPS6123778B2 JPS6123778B2 JP53022840A JP2284078A JPS6123778B2 JP S6123778 B2 JPS6123778 B2 JP S6123778B2 JP 53022840 A JP53022840 A JP 53022840A JP 2284078 A JP2284078 A JP 2284078A JP S6123778 B2 JPS6123778 B2 JP S6123778B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- bis
- trimethylsilyloxy
- hydroxy
- methyl
- 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 trialkylsilyl halide Chemical class 0.000 claims description 74
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WOPKYMRPOKFYNI-UHFFFAOYSA-N 2-hydroxycyclopent-2-en-1-one Chemical compound OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910000497 Amalgam Inorganic materials 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 239000001837 2-hydroxy-3-methylcyclopent-2-en-1-one Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006657 acyloin condensation reaction Methods 0.000 description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AGLAOVULPBEAOD-UHFFFAOYSA-N trimethyl-(2-trimethylsilyloxycyclodecen-1-yl)oxysilane Chemical compound C[Si](C)(C)OC1=C(O[Si](C)(C)C)CCCCCCCC1 AGLAOVULPBEAOD-UHFFFAOYSA-N 0.000 description 3
- CJBPIWYGBPOITC-UHFFFAOYSA-N trimethyl-(2-trimethylsilyloxycyclopenten-1-yl)oxysilane Chemical compound C[Si](C)(C)OC1=C(O[Si](C)(C)C)CCC1 CJBPIWYGBPOITC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxycyclohex-2-en-1-one Chemical compound OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 2
- HUAUJXQTUVPKLM-UHFFFAOYSA-N 2-methylpentanedioyl dichloride Chemical compound ClC(=O)C(C)CCC(Cl)=O HUAUJXQTUVPKLM-UHFFFAOYSA-N 0.000 description 2
- GQBMCHFBQGIJGX-UHFFFAOYSA-N 3-tert-butyl-2-hydroxycyclopent-2-en-1-one Chemical compound CC(C)(C)C1=C(O)C(=O)CC1 GQBMCHFBQGIJGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UJGPNLWJDSIACI-UHFFFAOYSA-N hexanedioyl dibromide Chemical compound BrC(=O)CCCCC(Br)=O UJGPNLWJDSIACI-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YKQGJUUJUGPEQD-UHFFFAOYSA-N trimethyl-(2-trimethylsilyloxycyclohexen-1-yl)oxysilane Chemical compound C[Si](C)(C)OC1=C(O[Si](C)(C)C)CCCC1 YKQGJUUJUGPEQD-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical compound OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 description 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 description 1
- NDSGOBVTOHVLGW-UHFFFAOYSA-N 2-ethylhexanedioyl dichloride Chemical compound CCC(C(Cl)=O)CCCC(Cl)=O NDSGOBVTOHVLGW-UHFFFAOYSA-N 0.000 description 1
- ATFKMZIKSMAHHG-UHFFFAOYSA-N 2-ethylpentanedioyl dibromide Chemical compound CCC(C(Br)=O)CCC(Br)=O ATFKMZIKSMAHHG-UHFFFAOYSA-N 0.000 description 1
- YMMYOFCECDLEPC-UHFFFAOYSA-N 2-ethylpentanedioyl dichloride Chemical compound CCC(C(Cl)=O)CCC(Cl)=O YMMYOFCECDLEPC-UHFFFAOYSA-N 0.000 description 1
- SLJHBSPMMSIDFJ-UHFFFAOYSA-N 2-methylheptanedioyl dichloride Chemical compound ClC(=O)C(C)CCCCC(Cl)=O SLJHBSPMMSIDFJ-UHFFFAOYSA-N 0.000 description 1
- UYAZSFMGCJMZOY-UHFFFAOYSA-N 2-methylhexanedioyl dichloride Chemical compound ClC(=O)C(C)CCCC(Cl)=O UYAZSFMGCJMZOY-UHFFFAOYSA-N 0.000 description 1
- FNJKVLNAINNDOE-UHFFFAOYSA-N 2-methyloctanedioyl dichloride Chemical compound ClC(=O)C(C)CCCCCC(Cl)=O FNJKVLNAINNDOE-UHFFFAOYSA-N 0.000 description 1
- UVZULAOEEVYKIC-UHFFFAOYSA-N 2-propylhexanedioyl dichloride Chemical compound CCCC(C(Cl)=O)CCCC(Cl)=O UVZULAOEEVYKIC-UHFFFAOYSA-N 0.000 description 1
- SAOPBTOIBJXDSR-UHFFFAOYSA-N 3-hexylcyclohex-2-en-1-one Chemical compound CCCCCCC1=CC(=O)CCC1 SAOPBTOIBJXDSR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JHPYUQSNTXJHAF-UHFFFAOYSA-N CCCCCCC1=C(O)C(=O)CCC1 Chemical compound CCCCCCC1=C(O)C(=O)CCC1 JHPYUQSNTXJHAF-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XKVBLDFHCUMPDO-UHFFFAOYSA-N OC1=CCCCCCCCC1=O Chemical compound OC1=CCCCCCCCC1=O XKVBLDFHCUMPDO-UHFFFAOYSA-N 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 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
- 235000013361 beverage Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- AVDUEHWPPXIAEB-UHFFFAOYSA-N chloro-ethyl-dimethylsilane Chemical compound CC[Si](C)(C)Cl AVDUEHWPPXIAEB-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- QVGANFDBDBSNPV-UHFFFAOYSA-N cyclodecen-1-yloxy(trimethyl)silane Chemical compound C[Si](C)(C)OC1=CCCCCCCCC1 QVGANFDBDBSNPV-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- YQAGVUODRGLPSR-UHFFFAOYSA-N decanedioyl dibromide Chemical compound BrC(=O)CCCCCCCCC(Br)=O YQAGVUODRGLPSR-UHFFFAOYSA-N 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- YVHINPHWBQIAEH-UHFFFAOYSA-N heptanedioyl dibromide Chemical compound BrC(=O)CCCCCC(Br)=O YVHINPHWBQIAEH-UHFFFAOYSA-N 0.000 description 1
- LVIMBOHJGMDKEJ-UHFFFAOYSA-N heptanedioyl dichloride Chemical compound ClC(=O)CCCCCC(Cl)=O LVIMBOHJGMDKEJ-UHFFFAOYSA-N 0.000 description 1
- WLDRPCCNZOIMIR-UHFFFAOYSA-N hexanedioyl diiodide Chemical compound IC(=O)CCCCC(I)=O WLDRPCCNZOIMIR-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- HGEVGSTXQGZPCL-UHFFFAOYSA-N nonanedioyl dichloride Chemical compound ClC(=O)CCCCCCCC(Cl)=O HGEVGSTXQGZPCL-UHFFFAOYSA-N 0.000 description 1
- FVENDMFTYXWGLT-UHFFFAOYSA-N octanedioyl dibromide Chemical compound BrC(=O)CCCCCCC(Br)=O FVENDMFTYXWGLT-UHFFFAOYSA-N 0.000 description 1
- STRJPIQDBSJULU-UHFFFAOYSA-N octanedioyl diiodide Chemical compound IC(=O)CCCCCCC(I)=O STRJPIQDBSJULU-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- PHLZDCSVSDSPPH-UHFFFAOYSA-N pentanedioyl dibromide Chemical compound BrC(=O)CCCC(Br)=O PHLZDCSVSDSPPH-UHFFFAOYSA-N 0.000 description 1
- SXALEKVULPPIRA-UHFFFAOYSA-N pentanedioyl diiodide Chemical compound IC(=O)CCCC(I)=O SXALEKVULPPIRA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SMXSTMQUCITNSC-UHFFFAOYSA-N trimethyl-(2-trimethylsilylcyclopenten-1-yl)silane Chemical compound C[Si](C)(C)C1=C([Si](C)(C)C)CCC1 SMXSTMQUCITNSC-UHFFFAOYSA-N 0.000 description 1
- KPHYVCXSNQKZHW-UHFFFAOYSA-N trimethyl-(2-trimethylsilyloxycycloocten-1-yl)oxysilane Chemical compound C[Si](C)(C)OC1=C(O[Si](C)(C)C)CCCCCC1 KPHYVCXSNQKZHW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2284078A JPS54117441A (en) | 1978-03-02 | 1978-03-02 | Preparation of 2-hydroxy-2-cycloalken-1-ones and their intermediates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2284078A JPS54117441A (en) | 1978-03-02 | 1978-03-02 | Preparation of 2-hydroxy-2-cycloalken-1-ones and their intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54117441A JPS54117441A (en) | 1979-09-12 |
| JPS6123778B2 true JPS6123778B2 (de) | 1986-06-07 |
Family
ID=12093894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2284078A Granted JPS54117441A (en) | 1978-03-02 | 1978-03-02 | Preparation of 2-hydroxy-2-cycloalken-1-ones and their intermediates |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54117441A (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592287B (zh) * | 2013-10-30 | 2017-09-22 | 新亚强硅化学股份有限公司 | 1,2‑双三甲基硅氧基环丁烯及其制备工艺 |
| CN104592284B (zh) * | 2013-10-30 | 2017-09-22 | 新亚强硅化学股份有限公司 | 1,2‑双三甲基硅氧基环己烯及其制备工艺 |
| CN104592285B (zh) * | 2013-10-30 | 2017-09-22 | 新亚强硅化学股份有限公司 | 1,2‑双三甲基硅氧基环戊烯及其制备工艺 |
| DE102015221529A1 (de) * | 2015-11-03 | 2017-05-04 | Cht R. Beitlich Gmbh | Kontinuierliches Verfahren für Reaktionen mit feinteiligen Alkalimetall-Dispersionen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1352460A (en) * | 1972-06-02 | 1974-05-08 | Pfizer | 2-hydroxy-3,5-diethylenecyclopeht-2-en-1-one and its use as a flavouring agent |
-
1978
- 1978-03-02 JP JP2284078A patent/JPS54117441A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1352460A (en) * | 1972-06-02 | 1974-05-08 | Pfizer | 2-hydroxy-3,5-diethylenecyclopeht-2-en-1-one and its use as a flavouring agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54117441A (en) | 1979-09-12 |
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