JPS58194842A

JPS58194842A - ニトロビニルフエノ−ル類の合成法

ニトロビニルフエノ−ル類の合成法

Info

Publication number: JPS58194842A
Authority: JP; Japan
Prior art keywords: nitromethane; haloform; cyclodextrin; derivative; derivatives
Prior art date: 1982-05-07
Legal status : Granted

Application number

JP7636782A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6313425B2 (enrdf_load_stackoverflow

Inventor

Hidefumi Hirai

平井　英史

Makoto Komiyama

真小宮山

Current Assignee

Individual

Original Assignee

Individual

Priority date

1982-05-07

Filing date

1982-05-07

Publication date

1983-11-12

1982-05-07 Application filed by Individual filed Critical Individual

1982-05-07 Priority to JP7636782A priority Critical patent/JPS58194842A/ja

1983-11-12 Publication of JPS58194842A publication Critical patent/JPS58194842A/ja

1988-03-25 Publication of JPS6313425B2 publication Critical patent/JPS6313425B2/ja

Status Granted legal-status Critical Current

Links

PMDYAIGGZBRBFX-UHFFFAOYSA-N 2-(2-nitroethenyl)phenol Chemical class OC1=CC=CC=C1C=C[N+]([O-])=O PMDYAIGGZBRBFX-UHFFFAOYSA-N 0.000 title claims description 12
230000015572 biosynthetic process Effects 0.000 title description 3
238000003786 synthesis reaction Methods 0.000 title description 3
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 12
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 11
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
239000003054 catalyst Substances 0.000 claims abstract 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000243 solution Substances 0.000 abstract description 8
239000003905 agrochemical Substances 0.000 abstract description 2
239000007864 aqueous solution Substances 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
239000004599 antimicrobial Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 15
239000000047 product Substances 0.000 description 9
238000000034 method Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000001116 FEMA 4028 Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
235000011175 beta-cyclodextrine Nutrition 0.000 description 2
229960004853 betadex Drugs 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
229940043377 alpha-cyclodextrin Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1