UST988010I4 - Process for preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate - Google Patents
Process for preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate Download PDFInfo
- Publication number
- UST988010I4 UST988010I4 US06/016,851 US1685179A UST988010I4 US T988010 I4 UST988010 I4 US T988010I4 US 1685179 A US1685179 A US 1685179A US T988010 I4 UST988010 I4 US T988010I4
- Authority
- US
- United States
- Prior art keywords
- nitrobenzoate
- preparing
- psig
- temperature
- pressure
- 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.)
- Pending
Links
- -1 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 abstract 1
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 abstract 1
- 238000011021 bench scale process Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- JGBJHRKCUKTQOE-UHFFFAOYSA-N methyl 5-chloro-2-nitrobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O JGBJHRKCUKTQOE-UHFFFAOYSA-N 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- BYEJYKXXMSURIM-UHFFFAOYSA-M potassium;5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound [K+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 BYEJYKXXMSURIM-UHFFFAOYSA-M 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- 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
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process of preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate such as a process for preparing methyl 5-(2',4'-dichlorophenoxy)-2-nitrobenzoate by the coupling reaction of methyl 2-nitro-5-chlorobenzoate with the potassium salt of 2,4-dichlorophenol in dimethylformamide solvent to produce a reaction product mixture containing desired ester product and byproduct potassium 5-(2',4'-dichlorophenoxy)-2-nitrobenzoate. The yield of desired ester product is increased by a process that comprises reacting said reaction product mixture in situ, with methyl chloride at a pressure of about 440 mm. Hg. to about 50 psig., for between about 0.5 hour and about 4 hours, and at a temperature between about 75° C. and about 105° C. In a specific embodiment the process is carried out on bench scale at a temperature of between about 75° C. and about 100° C. and at a pressure of between about 10 psig. and about 50 psig. In another specific embodiment the process is carried out on plant scale at a temperature of between about 75° C. and about 105° C. and at a pressure of between about 440 mm. Hg. and about 760 mm. Hg.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/016,851 UST988010I4 (en) | 1978-05-05 | 1979-03-02 | Process for preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90327578A | 1978-05-05 | 1978-05-05 | |
| US06/016,851 UST988010I4 (en) | 1978-05-05 | 1979-03-02 | Process for preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US90327578A Continuation-In-Part | 1978-05-05 | 1978-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UST988010I4 true UST988010I4 (en) | 1979-11-06 |
Family
ID=26689139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/016,851 Pending UST988010I4 (en) | 1978-05-05 | 1979-03-02 | Process for preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | UST988010I4 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395570A (en) | 1981-11-16 | 1983-07-26 | Rohm And Haas Company | Preparation of 5-(2-halo-4-trifluoromethylphenoxy)-2-nitrobenzoic acid and salts and esters and amides |
-
1979
- 1979-03-02 US US06/016,851 patent/UST988010I4/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395570A (en) | 1981-11-16 | 1983-07-26 | Rohm And Haas Company | Preparation of 5-(2-halo-4-trifluoromethylphenoxy)-2-nitrobenzoic acid and salts and esters and amides |
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