BE565282A

BE565282A -

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Publication number: BE565282A
Authority: BE; Belgium
Prior art keywords: methyl; group; tetrahydrofuran; oxo; converted
Prior art date

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English (en)

French (fr)

Publication of BE565282A publication Critical patent/BE565282A/fr

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-1 2-methyl-3-hydroxy-5-dimethylaminomethyl-tetrahydrofuran lithium aluminum hydride Chemical compound 0.000 claims description 22
238000000034 method Methods 0.000 claims description 14
125000004043 oxo group Chemical group O=* 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000000468 ketone group Chemical group 0.000 claims description 9
MQZOYKWIDAOENK-UHFFFAOYSA-N 5-methyl-4-oxooxolane-2-carboxylic acid Chemical compound CC1OC(C(O)=O)CC1=O MQZOYKWIDAOENK-UHFFFAOYSA-N 0.000 claims description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000004036 acetal group Chemical group 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 claims description 6
YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical class NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 claims description 5
238000006359 acetalization reaction Methods 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
229910052987 metal hydride Inorganic materials 0.000 claims description 4
150000004681 metal hydrides Chemical class 0.000 claims description 4
239000007868 Raney catalyst Substances 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
RYHWIGJYXWKNHY-UHFFFAOYSA-N 5-(aminomethyl)-2-methyloxolan-3-ol Chemical compound CC1OC(CN)CC1O RYHWIGJYXWKNHY-UHFFFAOYSA-N 0.000 claims description 2
GQXOOSCWCGTYCS-UHFFFAOYSA-N CC1OC(C(=O)N(C)C)CC1O Chemical compound CC1OC(C(=O)N(C)C)CC1O GQXOOSCWCGTYCS-UHFFFAOYSA-N 0.000 claims description 2
COBBZOXSSFQTKE-UHFFFAOYSA-N CC1OC(CC1=O)CN Chemical class CC1OC(CC1=O)CN COBBZOXSSFQTKE-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
ZWCFPVVHRISJNF-UHFFFAOYSA-N 4-hydroxy-5-methyloxolane-2-carboxylic acid Chemical compound CC1OC(C(O)=O)CC1O ZWCFPVVHRISJNF-UHFFFAOYSA-N 0.000 claims 1
AKRZXLWSUAUMSP-UHFFFAOYSA-N CC1OC(CO)CC1=O Chemical compound CC1OC(CO)CC1=O AKRZXLWSUAUMSP-UHFFFAOYSA-N 0.000 claims 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000012022 methylating agents‎ Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
238000009835 boiling Methods 0.000 description 12
239000000047 product Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000004821 distillation Methods 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
150000001241 acetals Chemical class 0.000 description 6
239000000155 melt Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
ZTZMUUSDSRMEDM-UHFFFAOYSA-N methyl 5-methyl-4-oxooxolane-2-carboxylate Chemical compound COC(=O)C1CC(=O)C(C)O1 ZTZMUUSDSRMEDM-UHFFFAOYSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000126 substance Substances 0.000 description 5
230000009466 transformation Effects 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
235000011118 potassium hydroxide Nutrition 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
UQOFGTXDASPNLL-UHFFFAOYSA-N (2s,4r,5s)-muscarine Chemical compound CC1OC(C[N+](C)(C)C)CC1O UQOFGTXDASPNLL-UHFFFAOYSA-N 0.000 description 2
WUOOMJSTTFTWGG-UHFFFAOYSA-N (4,4-dimethoxy-5-methyloxolan-2-yl)methanol Chemical compound CC1OC(CC1(OC)OC)CO WUOOMJSTTFTWGG-UHFFFAOYSA-N 0.000 description 2
FTTIZABOGGBXKB-UHFFFAOYSA-N (4,4-dimethoxy-5-methyloxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound CC1OC(CC1(OC)OC)COS(=O)(=O)C1=CC=C(C)C=C1 FTTIZABOGGBXKB-UHFFFAOYSA-N 0.000 description 2
WGWHQILKSZRLDQ-UHFFFAOYSA-N 4,4-dimethoxy-N,N,5-trimethyloxolane-2-carboxamide Chemical compound CC1OC(CC1(OC)OC)C(=O)N(C)C WGWHQILKSZRLDQ-UHFFFAOYSA-N 0.000 description 2
VTRXZONXIUOARD-UHFFFAOYSA-N CC1OC(CC1(OC)OC)C(=O)OC Chemical compound CC1OC(CC1(OC)OC)C(=O)OC VTRXZONXIUOARD-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910021607 Silver chloride Inorganic materials 0.000 description 2
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 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
238000006114 decarboxylation reaction Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
WUFRNEJYZWHXLC-UHFFFAOYSA-M (4-hydroxy-5-methyloxolan-2-yl)methyl-trimethylazanium;chloride Chemical compound [Cl-].CC1OC(C[N+](C)(C)C)CC1O WUFRNEJYZWHXLC-UHFFFAOYSA-M 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical class CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
WOLOBPUZOUBNCH-UHFFFAOYSA-N 5-(iodomethyl)-3,3-dimethoxy-2-methyloxolane Chemical compound COC1(OC)CC(CI)OC1C WOLOBPUZOUBNCH-UHFFFAOYSA-N 0.000 description 1
RRJMVBOQGJYNPF-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-2-methyloxolan-3-ol Chemical compound CC1OC(CN(C)C)CC1O RRJMVBOQGJYNPF-UHFFFAOYSA-N 0.000 description 1
ZFZWXIOZZVTDFD-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-2-methyloxolan-3-one Chemical compound CC1OC(CN(C)C)CC1=O ZFZWXIOZZVTDFD-UHFFFAOYSA-N 0.000 description 1
241000134914 Amanita muscaria Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UCOIECPRWIJUMK-UHFFFAOYSA-N CC1OC(CC1(OC)OC)CCl Chemical compound CC1OC(CC1(OC)OC)CCl UCOIECPRWIJUMK-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 description 1
SFZIGYHGVHQSCK-UHFFFAOYSA-N N,N,5-trimethyl-4-oxooxolane-2-carboxamide Chemical compound CC1OC(CC1=O)C(=O)N(C)C SFZIGYHGVHQSCK-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ZFVWBUVYNPLIIS-UHFFFAOYSA-N Tetrahydro-2-methyl-3-furanol Chemical compound CC1OCCC1O ZFVWBUVYNPLIIS-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940107816 ammonium iodide Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1