IL90703A - Method of preparing n-n-propyl-n-2-(2,4,6-trichlorophenoxy)-ethyl amine - Google Patents
Method of preparing n-n-propyl-n-2-(2,4,6-trichlorophenoxy)-ethyl amineInfo
- Publication number
- IL90703A IL90703A IL9070389A IL9070389A IL90703A IL 90703 A IL90703 A IL 90703A IL 9070389 A IL9070389 A IL 9070389A IL 9070389 A IL9070389 A IL 9070389A IL 90703 A IL90703 A IL 90703A
- Authority
- IL
- Israel
- Prior art keywords
- chloride
- phenoxy
- stage
- accordance
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- CLFQSOIBYICELN-UHFFFAOYSA-N n-[2-(2,4,6-trichlorophenoxy)ethyl]propan-1-amine Chemical compound CCCNCCOC1=C(Cl)C=C(Cl)C=C1Cl CLFQSOIBYICELN-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 18
- -1 tetraalkyl ammonium halide Chemical class 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004202 carbamide Substances 0.000 claims abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- VQUYNUJARXBNPK-UHFFFAOYSA-N 2-chloroethoxybenzene Chemical compound ClCCOC1=CC=CC=C1 VQUYNUJARXBNPK-UHFFFAOYSA-N 0.000 claims abstract description 11
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229960005323 phenoxyethanol Drugs 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229960003750 ethyl chloride Drugs 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 2
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- YNJGVSWHTYTTDC-UHFFFAOYSA-N 1,3,5-trichloro-2-(2-chloroethoxy)benzene Chemical compound ClCCOC1=C(Cl)C=C(Cl)C=C1Cl YNJGVSWHTYTTDC-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 7
- 239000005820 Prochloraz Substances 0.000 description 6
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- 150000004899 1,4-dioxins Chemical class 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000244317 Tillandsia usneoides Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL9070389A IL90703A (en) | 1989-06-21 | 1989-06-21 | Method of preparing n-n-propyl-n-2-(2,4,6-trichlorophenoxy)-ethyl amine |
| EP90111065A EP0403929B1 (de) | 1989-06-21 | 1990-06-12 | Verfahren zur Herstellung von als agrochemische Zwischenprodukte verwendbaren Phenoxyethern |
| DE69011976T DE69011976T2 (de) | 1989-06-21 | 1990-06-12 | Verfahren zur Herstellung von als agrochemische Zwischenprodukte verwendbaren Phenoxyethern. |
| AT90111065T ATE110709T1 (de) | 1989-06-21 | 1990-06-12 | Verfahren zur herstellung von als agrochemische zwischenprodukte verwendbaren phenoxyethern. |
| HU903823A HU207703B (en) | 1989-06-21 | 1990-06-13 | Process for producing n-/n-propyl/-/2-/2,4,6-trichloro-phenoxy/-ethyl/-amine |
| HU923862A HU208296B (en) | 1989-06-21 | 1990-06-13 | Method for producing 2-(2,4,6-trichloro-phenoxi)-ethyl-chloride |
| ZA904572A ZA904572B (en) | 1989-06-21 | 1990-06-13 | A method of preparing phenoxy ethers for use as agrochemical intermediates |
| US07/537,662 US5091577A (en) | 1989-06-21 | 1990-06-14 | Method of preparing fungicidal intermediates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL9070389A IL90703A (en) | 1989-06-21 | 1989-06-21 | Method of preparing n-n-propyl-n-2-(2,4,6-trichlorophenoxy)-ethyl amine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL90703A0 IL90703A0 (en) | 1990-01-18 |
| IL90703A true IL90703A (en) | 1994-10-07 |
Family
ID=11060074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9070389A IL90703A (en) | 1989-06-21 | 1989-06-21 | Method of preparing n-n-propyl-n-2-(2,4,6-trichlorophenoxy)-ethyl amine |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5091577A (de) |
| EP (1) | EP0403929B1 (de) |
| AT (1) | ATE110709T1 (de) |
| DE (1) | DE69011976T2 (de) |
| HU (2) | HU208296B (de) |
| IL (1) | IL90703A (de) |
| ZA (1) | ZA904572B (de) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1469772A (en) * | 1973-06-21 | 1977-04-06 | Boots Co Ltd | Fungicidal imidazole derivatives |
| US4504484A (en) * | 1982-11-04 | 1985-03-12 | Chevron Research Company | Certain N,N-di-substituted-pyridine carboxamides, fungicidal compositions and fungicidal method of use |
| GB8609904D0 (en) * | 1986-04-23 | 1986-05-29 | Fbc Ltd | Preparation of metal phenates |
| GB8714920D0 (en) * | 1987-06-25 | 1987-07-29 | Shell Int Research | Thiazole derivatives |
| DE3721158A1 (de) * | 1987-06-26 | 1989-01-05 | Krupp Gmbh | Werkzeugwechselsystem mit winkellagefixierung |
| FR2618146A1 (fr) * | 1987-07-17 | 1989-01-20 | Rhone Poulenc Chimie | Procede de preparation de trichloro-2,4,6 phenol |
-
1989
- 1989-06-21 IL IL9070389A patent/IL90703A/en not_active IP Right Cessation
-
1990
- 1990-06-12 AT AT90111065T patent/ATE110709T1/de not_active IP Right Cessation
- 1990-06-12 DE DE69011976T patent/DE69011976T2/de not_active Expired - Fee Related
- 1990-06-12 EP EP90111065A patent/EP0403929B1/de not_active Expired - Lifetime
- 1990-06-13 ZA ZA904572A patent/ZA904572B/xx unknown
- 1990-06-13 HU HU923862A patent/HU208296B/hu not_active IP Right Cessation
- 1990-06-13 HU HU903823A patent/HU207703B/hu not_active IP Right Cessation
- 1990-06-14 US US07/537,662 patent/US5091577A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE110709T1 (de) | 1994-09-15 |
| IL90703A0 (en) | 1990-01-18 |
| HU903823D0 (en) | 1990-11-28 |
| DE69011976D1 (de) | 1994-10-06 |
| HU207703B (en) | 1993-05-28 |
| EP0403929B1 (de) | 1994-08-31 |
| EP0403929A2 (de) | 1990-12-27 |
| US5091577A (en) | 1992-02-25 |
| DE69011976T2 (de) | 1995-03-30 |
| HU9203862D0 (en) | 1993-03-29 |
| ZA904572B (en) | 1991-03-27 |
| HUT53859A (en) | 1990-12-28 |
| EP0403929A3 (de) | 1992-02-26 |
| HU208296B (en) | 1993-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |