JPS59128368A - カルコゲン含有核置換基を有する安息香酸誘導体の製法 - Google Patents
カルコゲン含有核置換基を有する安息香酸誘導体の製法Info
- Publication number
- JPS59128368A JPS59128368A JP9883A JP9883A JPS59128368A JP S59128368 A JPS59128368 A JP S59128368A JP 9883 A JP9883 A JP 9883A JP 9883 A JP9883 A JP 9883A JP S59128368 A JPS59128368 A JP S59128368A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- chalcogen
- alkali metal
- metal hydroxide
- 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
- 229910052798 chalcogen Inorganic materials 0.000 title claims abstract description 19
- 150000001787 chalcogens Chemical class 0.000 title claims abstract description 15
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 25
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- 239000011669 selenium Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 30
- 239000002904 solvent Substances 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000005496 eutectics Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 230000008018 melting Effects 0.000 abstract description 2
- 238000002844 melting Methods 0.000 abstract description 2
- 238000005054 agglomeration Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 239000003905 agrochemical Substances 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 11
- 229940103494 thiosalicylic acid Drugs 0.000 description 11
- AJQLEJAVGARHGQ-UHFFFAOYSA-N dithiosalicylic acid Chemical compound OC1=CC=CC=C1C(S)=S AJQLEJAVGARHGQ-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 6
- -1 selenino Chemical group 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 229910052714 tellurium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KQOVQKHBCWQFCJ-UHFFFAOYSA-N 2-[(2-carboxyphenyl)diselanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1[Se][Se]C1=CC=CC=C1C(O)=O KQOVQKHBCWQFCJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241000951471 Citrus junos Species 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RQVWTMCUTHKGCM-UHFFFAOYSA-N S-Methyl benzenecarbothioate Chemical compound CSC(=O)C1=CC=CC=C1 RQVWTMCUTHKGCM-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009366 sericulture Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9883A JPS59128368A (ja) | 1983-01-04 | 1983-01-04 | カルコゲン含有核置換基を有する安息香酸誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9883A JPS59128368A (ja) | 1983-01-04 | 1983-01-04 | カルコゲン含有核置換基を有する安息香酸誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59128368A true JPS59128368A (ja) | 1984-07-24 |
| JPS6353985B2 JPS6353985B2 (enrdf_load_stackoverflow) | 1988-10-26 |
Family
ID=11464622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9883A Granted JPS59128368A (ja) | 1983-01-04 | 1983-01-04 | カルコゲン含有核置換基を有する安息香酸誘導体の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59128368A (enrdf_load_stackoverflow) |
-
1983
- 1983-01-04 JP JP9883A patent/JPS59128368A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6353985B2 (enrdf_load_stackoverflow) | 1988-10-26 |
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