JPS58185535A - ハロゲノ−３−フエニルブチルアルデヒド及びその製造方法 - Google Patents
ハロゲノ−３−フエニルブチルアルデヒド及びその製造方法Info
- Publication number
- JPS58185535A JPS58185535A JP6984782A JP6984782A JPS58185535A JP S58185535 A JPS58185535 A JP S58185535A JP 6984782 A JP6984782 A JP 6984782A JP 6984782 A JP6984782 A JP 6984782A JP S58185535 A JPS58185535 A JP S58185535A
- Authority
- JP
- Japan
- Prior art keywords
- water
- formula
- atom
- added
- mol
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical group NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 17
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract description 16
- 239000012954 diazonium Substances 0.000 abstract description 12
- 150000001989 diazonium salts Chemical class 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 229960003280 cupric chloride Drugs 0.000 abstract description 7
- 239000000543 intermediate Substances 0.000 abstract description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000005358 3-phenylpyrroles Chemical class 0.000 abstract 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6984782A JPS58185535A (ja) | 1982-04-26 | 1982-04-26 | ハロゲノ−３−フエニルブチルアルデヒド及びその製造方法 |
| US06/485,910 US4471126A (en) | 1982-04-26 | 1983-04-18 | Method for the production of 3-phenylpyrrole |
| KR1019830001722A KR860001335B1 (ko) | 1982-04-26 | 1983-04-23 | 3-페닐피롤 유도체의 제조방법 |
| EP83200592A EP0092890A1 (en) | 1982-04-26 | 1983-04-25 | Method for the production of 3-phenylpyrrole derivatives |
| ES521830A ES521830A0 (es) | 1982-04-26 | 1983-04-25 | Un metodo para la produccion de derivados de 3-fenilpirrol. |
| HU831433A HU190087B (en) | 1982-04-26 | 1983-04-26 | Process for preparing 3-phenyl-pyrrole derivatives |
| HU854800A HU193454B (en) | 1982-04-26 | 1983-04-26 | Process for producing 3-phenyl-butyraldehyde derivatives |
| IL68519A IL68519A (en) | 1982-04-26 | 1983-04-28 | Production of 3-phenylpyrrole derivatives,and novel 2,4-dichloro-3-phenylbutyraldehyde intermediates therefor |
| SU833657406A SU1225479A3 (ru) | 1982-04-26 | 1983-10-31 | Способ получени альдегидов |
| ES528633A ES8504703A1 (es) | 1982-04-26 | 1984-01-02 | Un metodo para la preparacion de nuevos derivados de fenilbutilaldehido |
| US06/615,328 US4532363A (en) | 1982-04-26 | 1984-05-30 | Phenylbutyraldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6984782A JPS58185535A (ja) | 1982-04-26 | 1982-04-26 | ハロゲノ−３−フエニルブチルアルデヒド及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58185535A true JPS58185535A (ja) | 1983-10-29 |
| JPH0336820B2 JPH0336820B2 (enrdf_load_html_response) | 1991-06-03 |
Family
ID=13414602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6984782A Granted JPS58185535A (ja) | 1982-04-26 | 1982-04-26 | ハロゲノ−３−フエニルブチルアルデヒド及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58185535A (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008196553A (ja) | 2007-02-09 | 2008-08-28 | Nok Corp | ボアプラグの装着構造 |
-
1982
- 1982-04-26 JP JP6984782A patent/JPS58185535A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0336820B2 (enrdf_load_html_response) | 1991-06-03 |
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