DE2242512C3 - Verfahren zur Herstellung von 4-Hydroxy-3-nitrobenzoesäurealkylestern - Google Patents
Verfahren zur Herstellung von 4-Hydroxy-3-nitrobenzoesäurealkylesternInfo
- Publication number
- DE2242512C3 DE2242512C3 DE19722242512 DE2242512A DE2242512C3 DE 2242512 C3 DE2242512 C3 DE 2242512C3 DE 19722242512 DE19722242512 DE 19722242512 DE 2242512 A DE2242512 A DE 2242512A DE 2242512 C3 DE2242512 C3 DE 2242512C3
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- alkyl esters
- preparation
- acid alkyl
- acid
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 9
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 6
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl 4-hydroxy-3-nitrobenzoate Chemical compound 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GNCWCTBHZCBXGL-UHFFFAOYSA-N methyl 4-hydroxy-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 GNCWCTBHZCBXGL-UHFFFAOYSA-N 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZDRLLQYICMQIOP-UHFFFAOYSA-N 2,3-dinitrooxybenzoic acid Chemical class [N+](=O)([O-])OC=1C(=C(C(=O)O)C=CC1)O[N+](=O)[O-] ZDRLLQYICMQIOP-UHFFFAOYSA-N 0.000 description 1
- MRBKRZAPGUCWOS-UHFFFAOYSA-N 3-amino-4-hydroxybenzoic acid Chemical class NC1=CC(C(O)=O)=CC=C1O MRBKRZAPGUCWOS-UHFFFAOYSA-N 0.000 description 1
- QRYSWXFQLFLJTC-UHFFFAOYSA-N 616-82-0 Chemical class OC(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 QRYSWXFQLFLJTC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722242512 DE2242512C3 (de) | 1972-08-30 | 1972-08-30 | Verfahren zur Herstellung von 4-Hydroxy-3-nitrobenzoesäurealkylestern |
| CH1225673A CH575905A5 (enExample) | 1972-08-30 | 1973-08-27 | |
| JP9580673A JPS4956944A (enExample) | 1972-08-30 | 1973-08-28 | |
| GB4068673A GB1390158A (en) | 1972-08-30 | 1973-08-29 | Preparation of 4-hydroxy-3-nitrobenzoic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722242512 DE2242512C3 (de) | 1972-08-30 | 1972-08-30 | Verfahren zur Herstellung von 4-Hydroxy-3-nitrobenzoesäurealkylestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2242512A1 DE2242512A1 (de) | 1974-04-11 |
| DE2242512B2 DE2242512B2 (de) | 1974-09-12 |
| DE2242512C3 true DE2242512C3 (de) | 1975-06-19 |
Family
ID=5854923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722242512 Expired DE2242512C3 (de) | 1972-08-30 | 1972-08-30 | Verfahren zur Herstellung von 4-Hydroxy-3-nitrobenzoesäurealkylestern |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS4956944A (enExample) |
| CH (1) | CH575905A5 (enExample) |
| DE (1) | DE2242512C3 (enExample) |
| GB (1) | GB1390158A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2004096750A1 (ja) * | 2003-05-02 | 2006-07-13 | 株式会社上野製薬応用研究所 | ３−ニトロ−４−アルコキシ安息香酸の製造方法 |
-
1972
- 1972-08-30 DE DE19722242512 patent/DE2242512C3/de not_active Expired
-
1973
- 1973-08-27 CH CH1225673A patent/CH575905A5/xx not_active IP Right Cessation
- 1973-08-28 JP JP9580673A patent/JPS4956944A/ja active Pending
- 1973-08-29 GB GB4068673A patent/GB1390158A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1390158A (en) | 1975-04-09 |
| JPS4956944A (enExample) | 1974-06-03 |
| DE2242512A1 (de) | 1974-04-11 |
| DE2242512B2 (de) | 1974-09-12 |
| CH575905A5 (enExample) | 1976-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2105687C2 (de) | Verfahren zur Herstellung von 3-substituierten 2,1,3-Benzothiadiazin-4-on-2,2-dioxiden | |
| DE3308922A1 (de) | Verfahren zur herstellung von fettsaeureestern der ascorbinsaeure | |
| EP0176026B1 (de) | Verfahren zur Herstellung von 2,4-Dichlor-5-fluor-benzoesäure | |
| DE2051269B2 (de) | Verfahren zur Herstellung von 3-Propiony !salicylsäure | |
| DE2835450C3 (de) | Verfahren zur Herstellung von 3,3-Bis-(4-dimethylaminophenyl)-6-dimethylaminophthalid (Kristallviolettlacton) | |
| DE2636423B1 (de) | Verfahren zur Herstellung von Anthranilsaeureestern | |
| DE2242512B2 (de) | Verfahren zur Herstellung von 4-Hydroxy-3-nitrobenzoesäurealkylestern | |
| EP0009796B1 (de) | Verfahren zur Herstellung von (Phenoxy- bzw. Benzyl)-phenoxypropionsäuremethylestern | |
| DE748621C (de) | Verfahren zum Bromieren von Phenolen und Naphtholen | |
| DE60210430T2 (de) | 2-Bromomethyl-6-methyl-benzoesäure und Verfahren zu ihrer Herstellung | |
| DE1768114A1 (de) | Verfahren zur Herstellung von alpha-Ketoglutarsaeure | |
| EP0021112A1 (de) | Verfahren zur Herstellung von 1,3-Dibrom-2,2-dimethylpropan-1,3-dicarbonsäure-derivaten sowie 1,3-Dibrom-2,2-dimethyl-propan-1,3-dicarbonsäure-dichlorid- und -chlorid-ester als neue Zwischenprodukte | |
| DE1111163B (de) | Verfahren zur Herstellung von Gemischen aus ª‡, ª‡, ª†- und ª‡, ª†, ª†-Trimethyladipinsaeure | |
| DE883436C (de) | Verfahren zur Herstellung eines 3, 22-Diacyloxy-bisnor-5, 7, 9 (11), 20 (22)-cholatetraenadditionsproduktes | |
| DE2112778B2 (de) | Verfahren zur Herstellung von 2-CyBn-S^Ae-IeITaChIOr- bzw. brombenzoesäurealkylestern | |
| DE2059296C3 (de) | Verfahren zur Herstellung von Estern der 3-Methylflavon-8-carbonsäure mit N-tert-Aminoalkoholen | |
| DE673485C (de) | Verfahren zur Darstellung von 1-Ascorbinsaeure | |
| DE2509481C3 (de) | Verfahren zur Herstellung von N-Acetylsalicylamid | |
| WO1991010635A1 (de) | Verfahren zur herstellung von 2,4,6-trimethylacetophenon | |
| DE2513952C2 (de) | Verfahren zur herstellung von monochlorbenzoesaeuren | |
| AT238383B (de) | Verfahren zur Herstellung einer therapeutisch wirksamen Steroidverbindung | |
| DE830792C (de) | Verfahren zur Herstellung von Acylaminoacetessigestern | |
| DD151624A1 (de) | Verfahren zur herstellung von 3-dimethylamino-2-cyanacrylsaeureestern | |
| DE1074572B (de) | Verfahren zur Herstellung von cychaliphatischen Tetraketonen | |
| DE1294970B (de) | Verfahren zur Herstellung von substituierten 6, 11-Dihydrodibenzo[b, e]-oxepin- bzw.-thiepin-11-onen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |