GB1591063A - Monoalkylation of dihydroxybenzenes - Google Patents
Monoalkylation of dihydroxybenzenes Download PDFInfo
- Publication number
- GB1591063A GB1591063A GB28983/77A GB2898377A GB1591063A GB 1591063 A GB1591063 A GB 1591063A GB 28983/77 A GB28983/77 A GB 28983/77A GB 2898377 A GB2898377 A GB 2898377A GB 1591063 A GB1591063 A GB 1591063A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- added
- methyl
- dihydroxybenzenes
- acetate
- 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
- 150000005205 dihydroxybenzenes Chemical class 0.000 title claims abstract description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000002168 alkylating agent Substances 0.000 claims abstract description 13
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- -1 hydroquinone chloroacetamide methanol Chemical compound 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 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 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- OITXOTZGDJLEBU-UHFFFAOYSA-N methyl 2-(4-hydroxyphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(O)C=C1 OITXOTZGDJLEBU-UHFFFAOYSA-N 0.000 claims description 4
- 239000001117 sulphuric acid Substances 0.000 claims description 4
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 3
- 229940106681 chloroacetic acid Drugs 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- PKGWLCZTTHWKIZ-UHFFFAOYSA-N 4-Hydroxypheoxyacetate Chemical compound OC(=O)COC1=CC=C(O)C=C1 PKGWLCZTTHWKIZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010013647 Drowning Diseases 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- UUYSCNGPNOYZMC-UHFFFAOYSA-N methyl 2-(4-hydroxyphenoxy)propanoate Chemical compound COC(=O)C(C)OC1=CC=C(O)C=C1 UUYSCNGPNOYZMC-UHFFFAOYSA-N 0.000 claims description 2
- XGDZEDRBLVIUMX-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1 XGDZEDRBLVIUMX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940080818 propionamide Drugs 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract description 4
- 239000002585 base Substances 0.000 abstract description 3
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-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
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001550206 Colla Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/547—Anthraquinones with aromatic ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28983/77A GB1591063A (en) | 1977-07-11 | 1977-07-11 | Monoalkylation of dihydroxybenzenes |
| DE19782824828 DE2824828A1 (de) | 1977-07-11 | 1978-06-06 | Verfahren zur herstellung von monoalkylierten dihydroxybenzolen |
| ES470998A ES470998A1 (es) | 1977-07-11 | 1978-06-21 | Procedimiento para preparar dihidroxibencenos monoalquilados |
| FR7819274A FR2397388B1 (enrdf_load_stackoverflow) | 1977-07-11 | 1978-06-28 | |
| JP8186478A JPS5419925A (en) | 1977-07-11 | 1978-07-05 | Process for preparing monoalkyldihydroxybenzene |
| CH744778A CH636332A5 (en) | 1977-07-11 | 1978-07-07 | Process for preparing monoalkylated dihydroxybenzenes |
| IT25505/78A IT1158883B (it) | 1977-07-11 | 1978-07-10 | Procedimento per monoalchilazione di di-idrossibenzoli |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28983/77A GB1591063A (en) | 1977-07-11 | 1977-07-11 | Monoalkylation of dihydroxybenzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1591063A true GB1591063A (en) | 1981-06-10 |
Family
ID=10284374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28983/77A Expired GB1591063A (en) | 1977-07-11 | 1977-07-11 | Monoalkylation of dihydroxybenzenes |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5419925A (enrdf_load_stackoverflow) |
| CH (1) | CH636332A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2824828A1 (enrdf_load_stackoverflow) |
| ES (1) | ES470998A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2397388B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1591063A (enrdf_load_stackoverflow) |
| IT (1) | IT1158883B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489207A (en) * | 1981-12-18 | 1984-12-18 | Basf Aktiengesellschaft | Preparation of 2-(hydroxyphenoxy)-carboxylates |
| EP0132367A3 (en) * | 1983-07-18 | 1985-05-15 | Eli Lilly And Company | Leukotriene antagonists |
| US4614814A (en) * | 1985-04-17 | 1986-09-30 | Stauffer Chemical Company | Monoalkylation of dihydroxy aromatic compounds |
| US4764521A (en) * | 1983-07-18 | 1988-08-16 | Eli Lilly And Company | Leukotriene antagonists and a method of use there as |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3240805A1 (de) * | 1982-11-05 | 1984-05-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von hydroxy-phenoxy-alkancarbonsaeuren |
| JPH0610153B2 (ja) * | 1984-10-26 | 1994-02-09 | 日産化学工業株式会社 | 光学活性２−（４−ヒドロキシフエノキシ）プロピオン酸の製造方法 |
| US5216024A (en) * | 1987-07-28 | 1993-06-01 | Baylor College Of Medicine | Cell growth inhibitors and methods of treating cancer and cell proliferative diseases |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370256A (en) * | 1940-01-09 | 1945-02-27 | Joseph B Niederl | Alkylated phenolic glycolic acids |
| US2593563A (en) * | 1949-05-02 | 1952-04-22 | Max N Huffman | Phloroglucinol derivatives |
| US3186843A (en) * | 1962-04-27 | 1965-06-01 | Polaroid Corp | Photographic developer containing hindered phenols |
| BE637443A (enrdf_load_stackoverflow) * | 1962-09-17 | |||
| US3860633A (en) * | 1969-06-11 | 1975-01-14 | Dow Chemical Co | 3,5-dihalo-4-carboxyalkoxy phenols and esters thereof |
-
1977
- 1977-07-11 GB GB28983/77A patent/GB1591063A/en not_active Expired
-
1978
- 1978-06-06 DE DE19782824828 patent/DE2824828A1/de not_active Withdrawn
- 1978-06-21 ES ES470998A patent/ES470998A1/es not_active Expired
- 1978-06-28 FR FR7819274A patent/FR2397388B1/fr not_active Expired
- 1978-07-05 JP JP8186478A patent/JPS5419925A/ja active Pending
- 1978-07-07 CH CH744778A patent/CH636332A5/de not_active IP Right Cessation
- 1978-07-10 IT IT25505/78A patent/IT1158883B/it active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489207A (en) * | 1981-12-18 | 1984-12-18 | Basf Aktiengesellschaft | Preparation of 2-(hydroxyphenoxy)-carboxylates |
| EP0132367A3 (en) * | 1983-07-18 | 1985-05-15 | Eli Lilly And Company | Leukotriene antagonists |
| US4764521A (en) * | 1983-07-18 | 1988-08-16 | Eli Lilly And Company | Leukotriene antagonists and a method of use there as |
| US4614814A (en) * | 1985-04-17 | 1986-09-30 | Stauffer Chemical Company | Monoalkylation of dihydroxy aromatic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7825505A0 (it) | 1978-07-10 |
| ES470998A1 (es) | 1979-02-01 |
| FR2397388B1 (enrdf_load_stackoverflow) | 1985-03-08 |
| DE2824828A1 (de) | 1979-02-01 |
| IT1158883B (it) | 1987-02-25 |
| CH636332A5 (en) | 1983-05-31 |
| FR2397388A1 (enrdf_load_stackoverflow) | 1979-02-09 |
| JPS5419925A (en) | 1979-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0477747B2 (enrdf_load_stackoverflow) | ||
| GB1591063A (en) | Monoalkylation of dihydroxybenzenes | |
| US2895992A (en) | Process for the production of benzoic | |
| SU919594A3 (ru) | Способ получени ангидридов изатовой кислоты | |
| DK171274B1 (da) | Fremgangsmåde til fremstilling af 3,3'-azo-bis-(6-hydroxy-benzoesyre) samt azobenzener som mellemprodukter dertil | |
| US5162584A (en) | Fluorobenzene derivatives | |
| KR100429082B1 (ko) | 1,2-벤즈이소티아졸린-3-온의제조방법 | |
| SU490290A3 (ru) | Способ получени производных пиримидин-6- ил -ацетоксиаминовой кислоты | |
| US4151210A (en) | Process for the production of phenylalkyl sulphones | |
| US3642882A (en) | Process for the production of nitroarylethermonocarboxylic acids and their esters | |
| US3417080A (en) | Sulfamylanthranilic acid amides and process for preparing them | |
| Sutter et al. | Dimethyl methylphosphonate as methylating reagent | |
| KR100491935B1 (ko) | 3-피페라지닐벤즈이소티아졸의제조방법 | |
| SU534182A3 (ru) | Способ получени серосодержащих производных триалкоксибензоиламинокарбоновой кислоты или их солей | |
| US4851575A (en) | Process for the preparation of 2-nitro-4-sulfamyldiphenylamine dyestuffs | |
| US4137238A (en) | Process for the preparation of 2-hydroxycarbazoles | |
| AU680989B2 (en) | Method of preparing 6-aryloxymethyl-1-hydroxy-4-methyl-2-pyridones | |
| EP0853077B1 (en) | Process for producing alkyl 3-amino-4-substituted benzoates | |
| US5315036A (en) | Process for the preparation of 2-aminobenzene-1,4-disulphonic acids and the new compound 6-chloro-2-aminobenzene-1,4-disulphonic acid | |
| US2749361A (en) | Cyclohexanecarboxamides | |
| JPH0676360B2 (ja) | ４−アルコキシ−，及び４−アリ−ルオキシ−３−アシルアミノフエニルカルボナ−ト類の合成法 | |
| KR940010887B1 (ko) | 형광성 4,4'-비스-벤즈-옥스(-티, -이미드)-아졸-2-일-스틸벤의 제조방법 | |
| US2724722A (en) | Process for the production of alpha-(o-aminoaryloxy)-fatty acids or their salts | |
| US4851158A (en) | N-alkyl-N-(aminophenylsulfonyl)-aminoalkylphosphonic acids | |
| JPH08268984A (ja) | ジフェニルアミンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |