SU202924A1 - - Google Patents

Info

Publication number

SU202924A1

SU202924A1 SU1066181A SU1066181A SU202924A1 SU 202924 A1 SU202924 A1 SU 202924A1 SU 1066181 A SU1066181 A SU 1066181A SU 1066181 A SU1066181 A SU 1066181A SU 202924 A1 SU202924 A1 SU 202924A1

Authority

SU

USSR - Soviet Union

Prior art keywords

acid

benzene

ether

hours

dihydrocoumarin

Prior art date

Links

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• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 7
• 150000001875 compounds Chemical class 0.000 description 5
• VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 4
• DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• 230000004071 biological effect Effects 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 238000000034 method Methods 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• -1 aryl amides Chemical class 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
• 239000004570 mortar (masonry) Substances 0.000 description 2
• RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
• 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 1
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 235000019568 aromas Nutrition 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical group C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 235000001671 coumarin Nutrition 0.000 description 1
• 229960000956 coumarin Drugs 0.000 description 1
• QLACLEPYLWLNTD-UHFFFAOYSA-N dihydrocinnamic acid Natural products COc1ccc(CCC(O)=O)c(O)c1OC QLACLEPYLWLNTD-UHFFFAOYSA-N 0.000 description 1
• 238000007336 electrophilic substitution reaction Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 229930005346 hydroxycinnamic acid Natural products 0.000 description 1
• DEDGUGJNLNLJSR-UHFFFAOYSA-N hydroxycinnamic acid group Chemical class OC(C(=O)O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 1
• 235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000005406 washing Methods 0.000 description 1