JPS58170729A - ヒドロキシカルコン類の合成法 - Google Patents
ヒドロキシカルコン類の合成法Info
- Publication number
- JPS58170729A JPS58170729A JP57051072A JP5107282A JPS58170729A JP S58170729 A JPS58170729 A JP S58170729A JP 57051072 A JP57051072 A JP 57051072A JP 5107282 A JP5107282 A JP 5107282A JP S58170729 A JPS58170729 A JP S58170729A
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- acetophenone
- derivative
- haloform
- hydroxychalcone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- UDOOPSJCRMKSGL-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one Chemical compound OC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 UDOOPSJCRMKSGL-UHFFFAOYSA-N 0.000 title claims description 10
- 238000010189 synthetic method Methods 0.000 title 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 23
- 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 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 16
- 239000001116 FEMA 4028 Substances 0.000 abstract description 5
- 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 5
- 235000011175 beta-cyclodextrine Nutrition 0.000 abstract description 5
- 229960004853 betadex Drugs 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 abstract 1
- 208000007107 Stomach Ulcer Diseases 0.000 abstract 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 abstract 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 201000005917 gastric ulcer Diseases 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- PWWCDTYUYPOAIU-DHZHZOJOSA-N 4-hydroxychalcone Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)C1=CC=CC=C1 PWWCDTYUYPOAIU-DHZHZOJOSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VFGLRVWAOAFUGZ-UHFFFAOYSA-N 2,3-dihydroxy-1,3-diphenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=O)C(O)=C(O)C1=CC=CC=C1 VFGLRVWAOAFUGZ-UHFFFAOYSA-N 0.000 description 2
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 2
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 235000005513 chalcones Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- UDOOPSJCRMKSGL-ZHACJKMWSA-N (e)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one Chemical compound OC1=CC=CC=C1\C=C\C(=O)C1=CC=CC=C1 UDOOPSJCRMKSGL-ZHACJKMWSA-N 0.000 description 1
- BKVQXAGWCJBYRG-UHFFFAOYSA-N 2,4-dihydroxy-5-(3-oxo-3-phenylprop-1-enyl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=CC(=O)C=2C=CC=CC=2)=C1O BKVQXAGWCJBYRG-UHFFFAOYSA-N 0.000 description 1
- VWHAAVRVLHCATE-UHFFFAOYSA-N 2-hydroxy-5-(3-oxo-3-phenylprop-1-enyl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=CC(=O)C=2C=CC=CC=2)=C1 VWHAAVRVLHCATE-UHFFFAOYSA-N 0.000 description 1
- JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 description 1
- OESPNJQIRRMMGU-UHFFFAOYSA-N 2-oxo-2-phenylethanesulfonic acid Chemical compound OS(=O)(=O)CC(=O)C1=CC=CC=C1 OESPNJQIRRMMGU-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- XOUUKYPTVGXKNX-UHFFFAOYSA-N 4-hydroxy-3-(3-oxo-3-phenylprop-1-enyl)benzoic acid Chemical compound OC(=O)C1=CC=C(O)C(C=CC(=O)C=2C=CC=CC=2)=C1 XOUUKYPTVGXKNX-UHFFFAOYSA-N 0.000 description 1
- 208000002699 Digestive System Neoplasms Diseases 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical class 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
- 150000002085 enols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-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)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 GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57051072A JPS58170729A (ja) | 1982-03-31 | 1982-03-31 | ヒドロキシカルコン類の合成法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57051072A JPS58170729A (ja) | 1982-03-31 | 1982-03-31 | ヒドロキシカルコン類の合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58170729A true JPS58170729A (ja) | 1983-10-07 |
| JPH0136815B2 JPH0136815B2 (enExample) | 1989-08-02 |
Family
ID=12876600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57051072A Granted JPS58170729A (ja) | 1982-03-31 | 1982-03-31 | ヒドロキシカルコン類の合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58170729A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985003701A1 (fr) * | 1984-02-14 | 1985-08-29 | Hidefumi Hirai | PROCEDE DE PREPARATION DE DERIVES DE PHENOL p-SUBSTITUE |
-
1982
- 1982-03-31 JP JP57051072A patent/JPS58170729A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| DIE MARKROMOLEKULARE CHEMIE RAPID DOMMUNICATIONS=1981 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985003701A1 (fr) * | 1984-02-14 | 1985-08-29 | Hidefumi Hirai | PROCEDE DE PREPARATION DE DERIVES DE PHENOL p-SUBSTITUE |
| US4663478A (en) * | 1984-02-14 | 1987-05-05 | Hidefuni Hirai | Process for producing a para-substituted phenol derivative |
| EP0173748B1 (en) * | 1984-02-14 | 1990-01-03 | HIRAI, Hidefumi | Process for producing substituted unsaturated six-membered ring compounds from phenol derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0136815B2 (enExample) | 1989-08-02 |
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