CH593227A5 - - Google Patents
Info
- Publication number
- CH593227A5 CH593227A5 CH493975A CH493975A CH593227A5 CH 593227 A5 CH593227 A5 CH 593227A5 CH 493975 A CH493975 A CH 493975A CH 493975 A CH493975 A CH 493975A CH 593227 A5 CH593227 A5 CH 593227A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ether
- dichloro
- cyclohexyl
- acid
- trichlorostyrene
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 8
- 150000005332 diethylamines Chemical class 0.000 claims description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 8
- 235000011152 sodium sulphate Nutrition 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- GXEUNRBWEAIPCN-UHFFFAOYSA-N 2-chloro-2-(3-chloro-4-cyclohexylphenyl)acetic acid Chemical compound ClC1=CC(C(Cl)C(=O)O)=CC=C1C1CCCCC1 GXEUNRBWEAIPCN-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 4
- GKPSJINFCPORHW-UHFFFAOYSA-N 2-(3-chloro-4-cyclohexylphenyl)-2-hydroxyacetic acid Chemical compound ClC1=CC(C(C(O)=O)O)=CC=C1C1CCCCC1 GKPSJINFCPORHW-UHFFFAOYSA-N 0.000 claims description 2
- 229910015844 BCl3 Inorganic materials 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 206010036030 Polyarthritis Diseases 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 230000001754 anti-pyretic effect Effects 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 208000030428 polyarticular arthritis Diseases 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA197,875A CA1028351A (fr) | 1974-04-19 | 1974-04-19 | SYNTHESE DE L'ACIDE .alpha.,3-DICHLORO-4-CYCLOHEXYLPHENYLACETIQUE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH593227A5 true CH593227A5 (fr) | 1977-11-30 |
Family
ID=4099742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH493975A CH593227A5 (fr) | 1974-04-19 | 1975-04-17 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS50151848A (fr) |
| AR (1) | AR205118A1 (fr) |
| CA (1) | CA1028351A (fr) |
| CH (1) | CH593227A5 (fr) |
| ES (1) | ES436013A1 (fr) |
| SE (1) | SE7504519L (fr) |
-
1974
- 1974-04-19 CA CA197,875A patent/CA1028351A/fr not_active Expired
-
1975
- 1975-01-01 AR AR258307A patent/AR205118A1/es active
- 1975-03-25 ES ES436013A patent/ES436013A1/es not_active Expired
- 1975-04-17 CH CH493975A patent/CH593227A5/de not_active IP Right Cessation
- 1975-04-18 SE SE7504519A patent/SE7504519L/xx not_active Application Discontinuation
- 1975-04-19 JP JP50048083A patent/JPS50151848A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES436013A1 (es) | 1977-01-01 |
| CA1028351A (fr) | 1978-03-21 |
| AR205118A1 (es) | 1976-04-05 |
| SE7504519L (sv) | 1975-10-20 |
| JPS50151848A (fr) | 1975-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |