JPS5855442A

JPS5855442A - パラヒドロキシベンズアルデヒドの合成法

パラヒドロキシベンズアルデヒドの合成法

Info

Publication number: JPS5855442A
Authority: JP; Japan
Prior art keywords: cyclodextrin; chloroform; phenol; reaction; selectivity
Prior art date: 1981-09-26
Legal status : Granted

Application number

JP15252481A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6232737B2 (enrdf_load_stackoverflow

Inventor

Hidefumi Hirai

平井　英史

Makoto Komiyama

真小宮山

Current Assignee

Individual

Original Assignee

Individual

Priority date

1981-09-26

Filing date

1981-09-26

Publication date

1983-04-01

1981-09-26 Application filed by Individual filed Critical Individual

1981-09-26 Priority to JP15252481A priority Critical patent/JPS5855442A/ja

1982-03-09 Priority to DE8282900665T priority patent/DE3274104D1/de

1982-03-09 Priority to DE8484112783T priority patent/DE3276858D1/de

1982-03-09 Priority to PCT/JP1982/000066 priority patent/WO1982003073A1/ja

1982-03-09 Priority to EP19840112783 priority patent/EP0158709B1/en

1982-03-09 Priority to EP82900665A priority patent/EP0073837B1/en

1983-04-01 Publication of JPS5855442A publication Critical patent/JPS5855442A/ja

1983-09-07 Priority to US06/530,157 priority patent/US4523037A/en

1987-07-16 Publication of JPS6232737B2 publication Critical patent/JPS6232737B2/ja

Status Granted legal-status Critical Current

Links

RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 title claims abstract description 21
238000000034 method Methods 0.000 title claims description 6
230000002194 synthesizing effect Effects 0.000 title description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 36
238000006243 chemical reaction Methods 0.000 claims abstract description 28
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 20
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 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 11
239000001116 FEMA 4028 Substances 0.000 abstract description 9
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 abstract description 9
235000011175 beta-cyclodextrine Nutrition 0.000 abstract description 9
229960004853 betadex Drugs 0.000 abstract description 9
239000007864 aqueous solution Substances 0.000 abstract description 7
229920001450 Alpha-Cyclodextrin Polymers 0.000 abstract description 6
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 abstract description 6
229940043377 alpha-cyclodextrin Drugs 0.000 abstract description 6
239000002994 raw material Substances 0.000 abstract description 5
239000003905 agrochemical Substances 0.000 abstract description 2
239000002246 antineoplastic agent Substances 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
239000000975 dye Substances 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
239000012159 carrier gas Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000001307 helium Substances 0.000 description 3
229910052734 helium Inorganic materials 0.000 description 3
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000581652 Hagenia abyssinica Species 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1