BE435169A

BE435169A -

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Publication number: BE435169A
Authority: BE; Belgium
Prior art keywords: series; solution; desc; groups; page number
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French (fr)

Publication of BE435169A publication Critical patent/BE435169A/fr

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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
230000003647 oxidation Effects 0.000 claims description 13
238000007254 oxidation reaction Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
238000002844 melting Methods 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
230000000875 corresponding Effects 0.000 claims description 9
239000011780 sodium chloride Substances 0.000 claims description 9
125000003172 aldehyde group Chemical group 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 3
230000003301 hydrolyzing Effects 0.000 claims description 3
230000001603 reducing Effects 0.000 claims description 3
239000003638 reducing agent Substances 0.000 claims description 3
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
238000010504 bond cleavage reaction Methods 0.000 claims description 2
238000005755 formation reaction Methods 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
238000005039 chemical industry Methods 0.000 claims 1
125000003700 epoxy group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000001590 oxidative Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 35
150000001875 compounds Chemical class 0.000 description 19
VUVGYHUDAICLFK-UHFFFAOYSA-N Perosmic oxide Chemical compound O=[Os](=O)(=O)=O VUVGYHUDAICLFK-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
229960000583 Acetic Acid Drugs 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000000859 sublimation Methods 0.000 description 5
230000001476 alcoholic Effects 0.000 description 4
-1 aromatic nitroso compounds Chemical class 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000008079 hexane Substances 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229940095076 benzaldehyde Drugs 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L Barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N N-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
XCRBXWCUXJNEFX-UHFFFAOYSA-N Peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 2
HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
238000007792 addition Methods 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000005712 crystallization Effects 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
229940067157 phenylhydrazine Drugs 0.000 description 2
239000001184 potassium carbonate Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane group Chemical group [C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 2
150000003128 pregnanes Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000001187 sodium carbonate Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical class C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 description 1
NTIXPPFPXLYJCT-CFTHBVFTSA-N (3S,5R,7S,8R,9S,10S,12R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol Chemical compound C([C@@H]1C[C@@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCCC(C)(C)O)C)[C@@]2(C)[C@H](O)C1 NTIXPPFPXLYJCT-CFTHBVFTSA-N 0.000 description 1
CPUKWYXYHPOQJH-RDQPJNLGSA-N (8R,9S,10S,13S,14S)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(=CC4)C=C)[C@@H]4[C@@H]3CCC21 CPUKWYXYHPOQJH-RDQPJNLGSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 1
JVVXIESDACOUKY-XGTQDSJUSA-N C(C)(=O)OC1CC2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)CC=O)C)[C@]2(CC1)C Chemical compound C(C)(=O)OC1CC2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)CC=O)C)[C@]2(CC1)C JVVXIESDACOUKY-XGTQDSJUSA-N 0.000 description 1
229940044172 CALCIUM FORMATE Drugs 0.000 description 1
CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
210000004940 Nucleus Anatomy 0.000 description 1
XQMLEHQSJUVWQI-APGZYCKESA-N O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4C=C)O)[C@@H]4[C@@H]3CCC2=C1 Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4C=C)O)[C@@H]4[C@@H]3CCC2=C1 XQMLEHQSJUVWQI-APGZYCKESA-N 0.000 description 1
WURFKUQACINBSI-UHFFFAOYSA-M Ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N Phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
KWIUHFFTVRNATP-UHFFFAOYSA-N Trimethylglycine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
239000004281 calcium formate Substances 0.000 description 1
235000019255 calcium formate Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atoms Chemical group C* 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 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
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
238000006385 ozonation reaction Methods 0.000 description 1
RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
238000000746 purification Methods 0.000 description 1
BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000009738 saturating Methods 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001131 transforming Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical group [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1