JPS6310142B2 - - Google Patents
Info
- Publication number
- JPS6310142B2 JPS6310142B2 JP17211883A JP17211883A JPS6310142B2 JP S6310142 B2 JPS6310142 B2 JP S6310142B2 JP 17211883 A JP17211883 A JP 17211883A JP 17211883 A JP17211883 A JP 17211883A JP S6310142 B2 JPS6310142 B2 JP S6310142B2
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- alkyl group
- formula
- acid
- acid derivative
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- -1 alkyl salicylic acid derivative Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012286 potassium permanganate Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- LNEAPIMQYSWIIK-UHFFFAOYSA-N 2-hydroxy-3-propanoylbenzaldehyde Chemical compound C(CC)(=O)C1=C(C(C=O)=CC=C1)O LNEAPIMQYSWIIK-UHFFFAOYSA-N 0.000 description 2
- BNKPFZVIJZNDLZ-UHFFFAOYSA-N 2-hydroxy-3-propanoylbenzoic acid Chemical compound CCC(=O)C1=CC=CC(C(O)=O)=C1O BNKPFZVIJZNDLZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WUTVVHZNZHDMNM-UHFFFAOYSA-N 2-hydroxy-1-phenylhex-4-en-1-one Chemical compound CC=CCC(O)C(=O)C1=CC=CC=C1 WUTVVHZNZHDMNM-UHFFFAOYSA-N 0.000 description 1
- AUVALWUPUHHNQV-UHFFFAOYSA-N 2-hydroxy-3-propylbenzoic acid Chemical compound CCCC1=CC=CC(C(O)=O)=C1O AUVALWUPUHHNQV-UHFFFAOYSA-N 0.000 description 1
- KWAGCWPFRUIZLG-UHFFFAOYSA-N 2-methoxy-3-propanoylbenzoic acid Chemical compound CCC(=O)C1=CC=CC(C(O)=O)=C1OC KWAGCWPFRUIZLG-UHFFFAOYSA-N 0.000 description 1
- QNRDKBXSCGZZFV-UHFFFAOYSA-N 2-methoxy-3-propylbenzoic acid Chemical compound CCCC1=CC=CC(C(O)=O)=C1OC QNRDKBXSCGZZFV-UHFFFAOYSA-N 0.000 description 1
- TVYRJQXMQNZLNO-UHFFFAOYSA-N 3-acetyl-2-hydroxybenzoic acid Chemical compound CC(=O)C1=CC=CC(C(O)=O)=C1O TVYRJQXMQNZLNO-UHFFFAOYSA-N 0.000 description 1
- DCARPOVHBQKEJV-UHFFFAOYSA-N 3-butyl-2-hydroxybenzoic acid Chemical compound CCCCC1=CC=CC(C(O)=O)=C1O DCARPOVHBQKEJV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SPIUTQOUKAMGCX-UHFFFAOYSA-N flavoxate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 SPIUTQOUKAMGCX-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- KLZFYWWPVQHTOY-UHFFFAOYSA-N methyl 2-hydroxy-3-propylbenzoate Chemical compound CCCC1=CC=CC(C(=O)OC)=C1O KLZFYWWPVQHTOY-UHFFFAOYSA-N 0.000 description 1
- HXAUZKXZXYPTOP-UHFFFAOYSA-N methyl 2-methoxy-3-propylbenzoate Chemical compound CCCC1=CC=CC(C(=O)OC)=C1OC HXAUZKXZXYPTOP-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17211883A JPS6064944A (ja) | 1983-09-20 | 1983-09-20 | アシル安息香酸誘導体およびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17211883A JPS6064944A (ja) | 1983-09-20 | 1983-09-20 | アシル安息香酸誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6064944A JPS6064944A (ja) | 1985-04-13 |
| JPS6310142B2 true JPS6310142B2 (enrdf_load_stackoverflow) | 1988-03-04 |
Family
ID=15935885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17211883A Granted JPS6064944A (ja) | 1983-09-20 | 1983-09-20 | アシル安息香酸誘導体およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6064944A (enrdf_load_stackoverflow) |
-
1983
- 1983-09-20 JP JP17211883A patent/JPS6064944A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6064944A (ja) | 1985-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH495981A (fr) | Procédé de préparation de dérivés carboxyliques de l'indoline-2 one | |
| US4851588A (en) | Novel process for the preparation of bronopol | |
| US4168280A (en) | Method for synthesis of 2-hydroxy-3-methyl cyclopent-2-ene-1-one | |
| JPS6310142B2 (enrdf_load_stackoverflow) | ||
| JPS5848532B2 (ja) | 準安定状態を有する安息香酸誘導体 | |
| JPS60246382A (ja) | アルキル２‐（２‐アシルアミドチアゾール‐４‐イル）‐２‐ブテノエード類およびそれらの製法 | |
| CN109836322B (zh) | 一种王浆酸的制备方法 | |
| JPH0147464B2 (enrdf_load_stackoverflow) | ||
| JP2824159B2 (ja) | （Ｓ）−（−）−α−ダマスコンの製法 | |
| US4220801A (en) | Process for making 4-aroyl-substituted phenoxyacetic acids | |
| KR910001236B1 (ko) | 2-(4-아미노페닐)-2-메틸프로필 알코올의 제조방법 | |
| JPH0129793B2 (enrdf_load_stackoverflow) | ||
| JPS6287599A (ja) | エリスロマイシン類のオキシム誘導体の製造法 | |
| JP2542843B2 (ja) | 新規なノルボルナン誘導体およびその製造法 | |
| JPS6241510B2 (enrdf_load_stackoverflow) | ||
| JPS61246176A (ja) | アミノラクトンの調製方法 | |
| FR2465735A1 (fr) | Composes intermediaires pour la preparation de derives de la morphine, et leur procede de preparation | |
| CH639085A5 (en) | Process for the preparation of xanthone derivatives | |
| JPH053874B2 (enrdf_load_stackoverflow) | ||
| JP2853929B2 (ja) | ２−クロロ−４，５−ジフルオロ−３−メトキシ安息香酸の製造方法 | |
| JP3132025B2 (ja) | （−）−ゴニオミチンの製造方法 | |
| JPH07252183A (ja) | フェノール誘導体の製造方法 | |
| JPH0150219B2 (enrdf_load_stackoverflow) | ||
| JPS588375B2 (ja) | プロピオン酸誘導体化合物 | |
| JPS60204772A (ja) | イソオキサゾール誘導体の調製方法 |