SU649307A3 - Способ получени о-оксиарилбензальдегидов - Google Patents
Способ получени о-оксиарилбензальдегидовInfo
- Publication number
- SU649307A3 SU649307A3 SU762430496A SU2430496A SU649307A3 SU 649307 A3 SU649307 A3 SU 649307A3 SU 762430496 A SU762430496 A SU 762430496A SU 2430496 A SU2430496 A SU 2430496A SU 649307 A3 SU649307 A3 SU 649307A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- weight
- parts
- water
- solution
- hours
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 9
- 239000010410 layer Substances 0.000 claims description 9
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 239000011790 ferrous sulphate Substances 0.000 claims description 7
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 7
- 238000004809 thin layer chromatography Methods 0.000 claims description 7
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 6
- 238000001030 gas--liquid chromatography Methods 0.000 claims description 6
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 5
- -1 4-methylphenylaminomethyl Chemical group 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004160 Ammonium persulphate Substances 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 claims 3
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 claims 3
- FYUJLFRLDGSXBN-UHFFFAOYSA-N 5-heptyl-2-hydroxybenzaldehyde Chemical compound CCCCCCCC1=CC=C(O)C(C=O)=C1 FYUJLFRLDGSXBN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 32
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 26
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- JYWIGMQDJSGOMD-UHFFFAOYSA-N 2-hydroxy-5-nonylbenzaldehyde Chemical compound CCCCCCCCCC1=CC=C(O)C(C=O)=C1 JYWIGMQDJSGOMD-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 229910000358 iron sulfate Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- WZDJIONLTAQKEN-UHFFFAOYSA-N 2-[(2-methoxyanilino)methyl]-4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C(CNC=2C(=CC=CC=2)OC)=C1 WZDJIONLTAQKEN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000005569 Iron sulphate Substances 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229930195143 oxyphenol Natural products 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51286/75A GB1563206A (en) | 1975-12-15 | 1975-12-15 | Process for the manufacture of o-hydroxyaryl aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU649307A3 true SU649307A3 (ru) | 1979-02-25 |
Family
ID=10459412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762430496A SU649307A3 (ru) | 1975-12-15 | 1976-12-14 | Способ получени о-оксиарилбензальдегидов |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4085146A (enExample) |
| JP (1) | JPS5273833A (enExample) |
| AU (1) | AU512663B2 (enExample) |
| BE (1) | BE848935A (enExample) |
| BR (1) | BR7608158A (enExample) |
| CA (1) | CA1087209A (enExample) |
| CH (1) | CH625497A5 (enExample) |
| DE (1) | DE2656880A1 (enExample) |
| FR (1) | FR2335484A1 (enExample) |
| GB (1) | GB1563206A (enExample) |
| IE (1) | IE43752B1 (enExample) |
| IT (1) | IT1064349B (enExample) |
| NL (1) | NL7613431A (enExample) |
| SU (1) | SU649307A3 (enExample) |
| ZA (1) | ZA767011B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4638096A (en) * | 1982-10-12 | 1987-01-20 | Henkel Corporation | Process of preparing hydroxyarylaldehydes and catalyst therefor |
| GB9108221D0 (en) * | 1991-04-18 | 1991-06-05 | Ici Plc | Compound preparation and use |
| US5879556A (en) * | 1995-01-25 | 1999-03-09 | Henkel Corporation | Method of recovering extractant |
| US5877355A (en) * | 1996-03-19 | 1999-03-02 | Henkel Corporation | 2-hydroxy-5-alkyl-beta-methylstyrene and process of preparing hydroxyarylaldehydes therefrom |
| US5976218A (en) * | 1996-05-10 | 1999-11-02 | Henkel Corporation | Process for the recovery of nickel |
| PE12199A1 (es) * | 1996-10-21 | 1999-03-04 | Henkel Corp | Soluciones concentradas de extractantes metalicos de oxima y metodo para formular las composiciones extractantes a partir de dichas soluciones |
| US6210647B1 (en) | 1996-12-23 | 2001-04-03 | Henkel Corporation | Process of recovery of metals from aqueous ammoniacal solutions employing an ammonia antagonist having only hydrogen bond acceptor properties |
| US5993757A (en) * | 1997-03-03 | 1999-11-30 | Henkel Corporation | Reoximation of metal extraction circuit organics |
| US6177055B1 (en) | 1998-09-14 | 2001-01-23 | Henkel Corporation | Process for extracting and recovering copper |
| US6342635B1 (en) | 1998-09-15 | 2002-01-29 | Henkel Corporation | Ketoximes, processes therefor, and copper extraction process |
| US6156280A (en) * | 1999-02-24 | 2000-12-05 | Henkel Corporation | Process for removing manganese from organic solutions of oximes and nickel ore treatment process |
| US6702872B1 (en) | 1999-07-08 | 2004-03-09 | Cognis Corporation | Processes for the recovery of copper from aqueous solutions containing nitrate ions |
| US6596053B2 (en) | 1999-07-08 | 2003-07-22 | Cognis Corporation | Processes for the recovery of copper from aqueous solutions containing nitrate ions |
| US6432167B1 (en) | 1999-07-08 | 2002-08-13 | Cognis Corporation | Processes for the recovery of copper from aqueous solutions containing nitrate ions |
| MXPA02001433A (es) | 1999-08-12 | 2002-07-02 | Cognis Corp | Metodo para saparar el cobre del hierro. |
| US6261526B1 (en) | 1999-08-12 | 2001-07-17 | Henkel Corporation | Nickel recovery process and compositions for use therein |
| US6242625B1 (en) | 1999-09-30 | 2001-06-05 | Henkel Corporation | Process for extracting copper values from copper containing ores |
| US6599414B1 (en) | 2001-08-07 | 2003-07-29 | Cognis Corporation | Solvent extraction processes for metal recovery |
| US20040258590A1 (en) * | 2003-05-15 | 2004-12-23 | Kordosky Gary A. | Method for extracting copper from leach solutions at elevated temperatures |
| US7256161B2 (en) * | 2003-11-13 | 2007-08-14 | Chevron Oronite Company Llc | Process for making group II metal carbonated, overbased Mannich condensation products of alkylphenols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR516995A (fr) * | 1919-02-18 | 1921-04-28 | Andre Weiss | Procédé de préparation des oxyaldéhydes et de leurs éthers |
| FR653975A (fr) * | 1927-07-30 | 1929-03-29 | Ig Farbenindustrie Ag | Procédé de fabrication d'oxyaldéhydes aromatiques |
| US2576064A (en) * | 1949-12-23 | 1951-11-20 | Dow Chemical Co | Production of 3-fluorosalicylaldehyde |
| US2576065A (en) * | 1949-12-23 | 1951-11-20 | Dow Chemical Co | Preparation of 3-fluorosalicylaldehyde |
| US3173956A (en) * | 1963-10-24 | 1965-03-16 | Dow Chemical Co | Process for making salicylaldehydes |
-
1975
- 1975-12-15 GB GB51286/75A patent/GB1563206A/en not_active Expired
-
1976
- 1976-11-22 IE IE2567/76A patent/IE43752B1/en not_active IP Right Cessation
- 1976-11-23 US US05/744,279 patent/US4085146A/en not_active Expired - Lifetime
- 1976-11-23 ZA ZA767011A patent/ZA767011B/xx unknown
- 1976-11-29 CA CA266,744A patent/CA1087209A/en not_active Expired
- 1976-11-30 BE BE172867A patent/BE848935A/xx not_active IP Right Cessation
- 1976-11-30 IT IT29933/76A patent/IT1064349B/it active
- 1976-12-01 AU AU20143/76A patent/AU512663B2/en not_active Expired
- 1976-12-02 NL NL7613431A patent/NL7613431A/xx not_active Application Discontinuation
- 1976-12-06 BR BR7608158A patent/BR7608158A/pt unknown
- 1976-12-14 CH CH1573276A patent/CH625497A5/de not_active IP Right Cessation
- 1976-12-14 FR FR7637646A patent/FR2335484A1/fr active Granted
- 1976-12-14 SU SU762430496A patent/SU649307A3/ru active
- 1976-12-15 DE DE19762656880 patent/DE2656880A1/de not_active Withdrawn
- 1976-12-15 JP JP51150702A patent/JPS5273833A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH625497A5 (enExample) | 1981-09-30 |
| IT1064349B (it) | 1985-02-18 |
| ZA767011B (en) | 1977-11-30 |
| AU2014376A (en) | 1978-06-08 |
| FR2335484B1 (enExample) | 1980-09-12 |
| JPS5273833A (en) | 1977-06-21 |
| IE43752B1 (en) | 1981-05-20 |
| GB1563206A (en) | 1980-03-19 |
| NL7613431A (nl) | 1977-06-17 |
| US4085146A (en) | 1978-04-18 |
| DE2656880A1 (de) | 1977-06-23 |
| FR2335484A1 (fr) | 1977-07-15 |
| BE848935A (fr) | 1977-05-31 |
| IE43752L (en) | 1977-06-15 |
| CA1087209A (en) | 1980-10-07 |
| AU512663B2 (en) | 1980-10-23 |
| BR7608158A (pt) | 1977-11-22 |
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