SU550981A3 - Способ получени производных 1,3-диоксана - Google Patents
Способ получени производных 1,3-диоксанаInfo
- Publication number
- SU550981A3 SU550981A3 SU2043815A SU2043815A SU550981A3 SU 550981 A3 SU550981 A3 SU 550981A3 SU 2043815 A SU2043815 A SU 2043815A SU 2043815 A SU2043815 A SU 2043815A SU 550981 A3 SU550981 A3 SU 550981A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dioxane
- cis
- fluorobenzyloxy
- methyl
- benzyloxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000000093 1,3-dioxanes Chemical class 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- -1 cyanalkyl Chemical group 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- WZKXQJURGRERJY-UHFFFAOYSA-N 2-[(2-fluorophenyl)methoxy]-2-methylpropane-1,3-diol Chemical compound OCC(C)(CO)OCC1=CC=CC=C1F WZKXQJURGRERJY-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical class C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 4
- UDIPIOHLDFSMLR-UHFFFAOYSA-N 2-phenylmethoxypropane-1,3-diol Chemical compound OCC(CO)OCC1=CC=CC=C1 UDIPIOHLDFSMLR-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- RPZCVZVTXRZDAZ-UHFFFAOYSA-N diethyl 2-[(2-fluorophenyl)methoxy]-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)OCC1=CC=CC=C1F RPZCVZVTXRZDAZ-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- GEASUTBFDRNQEF-UHFFFAOYSA-N 2-(chloromethyl)-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(CCl)OCC1OCC1=CC=CC=C1 GEASUTBFDRNQEF-UHFFFAOYSA-N 0.000 description 2
- WLSBXUTYJZHJDW-UHFFFAOYSA-N 2-ethyl-5-[(2-fluorophenyl)methoxy]-5-methyl-1,3-dioxane Chemical compound C1OC(CC)OCC1(C)OCC1=CC=CC=C1F WLSBXUTYJZHJDW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- QEHXDOJPVIHUDO-UHFFFAOYSA-N (2-fluorophenyl)methanol Chemical compound OCC1=CC=CC=C1F QEHXDOJPVIHUDO-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical group NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- PCYADPMXIILFTP-UHFFFAOYSA-N 1,1-diethoxy-2-methoxyethane Chemical compound CCOC(COC)OCC PCYADPMXIILFTP-UHFFFAOYSA-N 0.000 description 1
- CGDFUIJLIZDUCG-UHFFFAOYSA-N 1,3-dioxan-5-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1COCOC1 CGDFUIJLIZDUCG-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OMTBMVJQYXLWAE-UHFFFAOYSA-N 2,5-diethyl-5-[(2-fluorophenyl)methoxy]-1,3-dioxane Chemical compound C1OC(CC)OCC1(CC)OCC1=CC=CC=C1F OMTBMVJQYXLWAE-UHFFFAOYSA-N 0.000 description 1
- WXKWKNVAWSDNLG-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-5-phenylmethoxy-1,3-dioxane Chemical compound CCOC1=CC=CC=C1C1OCC(OCC=2C=CC=CC=2)CO1 WXKWKNVAWSDNLG-UHFFFAOYSA-N 0.000 description 1
- BWYHAHQMECAMAR-UHFFFAOYSA-N 2-(bromomethyl)-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(CBr)OCC1OCC1=CC=CC=C1 BWYHAHQMECAMAR-UHFFFAOYSA-N 0.000 description 1
- NUHDKJAUAXCWED-UHFFFAOYSA-N 2-(chloromethyl)-5-[(2-fluorophenyl)methoxy]-5-methyl-1,3-dioxane Chemical compound C=1C=CC=C(F)C=1COC1(C)COC(CCl)OC1 NUHDKJAUAXCWED-UHFFFAOYSA-N 0.000 description 1
- HDNRCMSNNPLGFO-UHFFFAOYSA-N 2-(furan-2-yl)-5-[(2-methylphenyl)methoxy]-1,3-dioxane Chemical compound CC1=CC=CC=C1COC1COC(C=2OC=CC=2)OC1 HDNRCMSNNPLGFO-UHFFFAOYSA-N 0.000 description 1
- UJBZRWXLUJWIEB-UHFFFAOYSA-N 2-(furan-2-yl)-5-phenylmethoxy-1,3-dioxane Chemical compound C=1C=CC=CC=1COC(CO1)COC1C1=CC=CO1 UJBZRWXLUJWIEB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- GLEDFKMOWGWMGL-UHFFFAOYSA-N 2-ethyl-2-[(2-fluorophenyl)methoxy]propane-1,3-diol Chemical compound CCC(CO)(CO)OCC1=CC=CC=C1F GLEDFKMOWGWMGL-UHFFFAOYSA-N 0.000 description 1
- QDCBEAGPHBHTKW-UHFFFAOYSA-N 2-ethyl-5-methylidene-1,3-dioxane Chemical compound CCC1OCC(=C)CO1 QDCBEAGPHBHTKW-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- WWFBJSHMAGGTSO-UHFFFAOYSA-N 2-methyl-2-phenyl-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(C)(C=2C=CC=CC=2)OCC1OCC1=CC=CC=C1 WWFBJSHMAGGTSO-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- YXFAFPDQHWFQSL-UHFFFAOYSA-N 4,4,7,7-tetramethyl-1,3-dioxepane Chemical compound CC1(C)CCC(C)(C)OCO1 YXFAFPDQHWFQSL-UHFFFAOYSA-N 0.000 description 1
- ZNTXHVJPXKUFOK-UHFFFAOYSA-N 5-[(2-fluorophenyl)methoxy]-2-(furan-2-yl)-1,3-dioxane Chemical compound FC1=CC=CC=C1COC1COC(C=2OC=CC=2)OC1 ZNTXHVJPXKUFOK-UHFFFAOYSA-N 0.000 description 1
- CWVCWKQSGCKPGT-UHFFFAOYSA-N 5-[(2-fluorophenyl)methoxy]-2-(methoxymethyl)-5-methyl-1,3-dioxane Chemical compound C1OC(COC)OCC1(C)OCC1=CC=CC=C1F CWVCWKQSGCKPGT-UHFFFAOYSA-N 0.000 description 1
- UAESGIBOJCAHQP-UHFFFAOYSA-N 5-phenylmethoxy-1,3-dioxane Chemical compound C=1C=CC=CC=1COC1COCOC1 UAESGIBOJCAHQP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- CSLQAXTUGPUBCW-UHFFFAOYSA-N diethyl 2-bromo-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(Br)C(=O)OCC CSLQAXTUGPUBCW-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18240071A | 1971-09-21 | 1971-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU550981A3 true SU550981A3 (ru) | 1977-03-15 |
Family
ID=22668306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2043815A SU550981A3 (ru) | 1971-09-21 | 1974-07-17 | Способ получени производных 1,3-диоксана |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT321299B (enExample) |
| BR (1) | BR7206555D0 (enExample) |
| CS (1) | CS177090B2 (enExample) |
| HU (1) | HU166087B (enExample) |
| PL (1) | PL83582B1 (enExample) |
| SU (1) | SU550981A3 (enExample) |
| ZA (1) | ZA725840B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2537320C1 (ru) * | 2013-08-07 | 2015-01-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" | Способ получения 5-(хлорметил)-5-(алкоксиметил)-1,3-диоксанов |
-
1972
- 1972-08-24 ZA ZA725840A patent/ZA725840B/xx unknown
- 1972-09-12 CS CS624772A patent/CS177090B2/cs unknown
- 1972-09-14 AT AT789172A patent/AT321299B/de not_active IP Right Cessation
- 1972-09-19 PL PL15781372A patent/PL83582B1/pl unknown
- 1972-09-20 HU HUFA000923 patent/HU166087B/hu unknown
- 1972-09-21 BR BR655572A patent/BR7206555D0/pt unknown
-
1974
- 1974-07-17 SU SU2043815A patent/SU550981A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2537320C1 (ru) * | 2013-08-07 | 2015-01-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" | Способ получения 5-(хлорметил)-5-(алкоксиметил)-1,3-диоксанов |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA725840B (en) | 1973-09-26 |
| PL83582B1 (en) | 1975-12-31 |
| CS177090B2 (enExample) | 1977-07-29 |
| HU166087B (enExample) | 1975-01-28 |
| AT321299B (de) | 1975-03-25 |
| BR7206555D0 (pt) | 1973-08-21 |
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