CA1052823A - Process for the preparation of cyclohexanediones-(1,3) - Google Patents
Process for the preparation of cyclohexanediones-(1,3)Info
- Publication number
- CA1052823A CA1052823A CA187,723A CA187723A CA1052823A CA 1052823 A CA1052823 A CA 1052823A CA 187723 A CA187723 A CA 187723A CA 1052823 A CA1052823 A CA 1052823A
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- pyranone
- dimethyl
- formula
- group
- 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 abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 150000003457 sulfones Chemical class 0.000 claims abstract description 5
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 229940113088 dimethylacetamide Drugs 0.000 claims description 4
- 150000003012 phosphoric acid amides Chemical class 0.000 claims description 4
- DOSOPEZOHKMQPJ-UHFFFAOYSA-N 6-methyl-3,4-dihydropyran-2-one Chemical compound CC1=CCCC(=O)O1 DOSOPEZOHKMQPJ-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ZRYLICPCUZPPBY-UHFFFAOYSA-N 5,5-dimethyl-6-methylideneoxan-2-one Chemical compound CC1(C)CCC(=O)OC1=C ZRYLICPCUZPPBY-UHFFFAOYSA-N 0.000 claims description 2
- CZEOXNDFAPPJHG-UHFFFAOYSA-N 5,6-dimethyl-3,4-dihydropyran-2-one Chemical compound CC1=C(C)OC(=O)CC1 CZEOXNDFAPPJHG-UHFFFAOYSA-N 0.000 claims description 2
- MPXKFZYJBIYPCM-UHFFFAOYSA-N 6-methyl-5-phenyl-3,4-dihydropyran-2-one Chemical compound C1CC(=O)OC(C)=C1C1=CC=CC=C1 MPXKFZYJBIYPCM-UHFFFAOYSA-N 0.000 claims description 2
- 229910000497 Amalgam Inorganic materials 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical group CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 abstract description 10
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- 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 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
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)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2261751A DE2261751C3 (de) | 1972-12-16 | 1972-12-16 | Verfahren zur Herstellung von Cyclohexandionen-(1,3) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052823A true CA1052823A (en) | 1979-04-17 |
Family
ID=5864636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA187,723A Expired CA1052823A (en) | 1972-12-16 | 1973-12-07 | Process for the preparation of cyclohexanediones-(1,3) |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3932510A (en:Method) |
| JP (1) | JPS4987649A (en:Method) |
| BE (1) | BE808733A (en:Method) |
| CA (1) | CA1052823A (en:Method) |
| CH (1) | CH611867A5 (en:Method) |
| DE (1) | DE2261751C3 (en:Method) |
| FR (1) | FR2210600B1 (en:Method) |
| GB (1) | GB1458980A (en:Method) |
| IT (1) | IT1001411B (en:Method) |
| NL (1) | NL7316928A (en:Method) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2450086C3 (de) * | 1974-10-22 | 1981-10-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Resorcinen aus δ -Ketocarbonsäuren oder ihren Lactonen |
| DE2504930C2 (de) * | 1975-02-06 | 1983-02-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 2,6,6- Trimethyl-cyclohex-2-en-1-on |
| DE2533920C2 (de) * | 1975-07-30 | 1982-12-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Resorcinen |
| US4371711A (en) * | 1979-05-30 | 1983-02-01 | Sumitomo Chemical Company, Limited | Process for producing 4-hydroxycyclopentenones |
| US4701539A (en) * | 1979-11-01 | 1987-10-20 | Fmc Corporation | 3,4-dihydro-4,4-dimethyl-2H-pyran-2-one, an insecticide intermediate |
| US4347386A (en) * | 1980-04-30 | 1982-08-31 | Sumitomo Chemical Company, Limited | Process for preparing cyclopentenolones |
| US4398043A (en) * | 1980-12-10 | 1983-08-09 | Sumitomo Chemical Company, Limited | Process for preparing cyclopentenolones |
| EP0065708A3 (de) * | 1981-05-21 | 1983-01-26 | Lonza Ag | Verfahren zur Herstellung von Dimedon |
| US5744648A (en) * | 1996-08-01 | 1998-04-28 | Hoechst Celanese Corporation | Process for the manufacture of 1, 3-cyclohexanedione |
| AU2003203479B2 (en) * | 2002-04-09 | 2005-10-06 | Syngenta Participations Ag | Process for the preparation of bicyclic diketone salts |
| AU2003203482B2 (en) * | 2002-04-09 | 2005-06-02 | Syngenta Participations Ag | Process for the preparation of cyclic diketones |
| EP1491951A3 (en) * | 2003-06-09 | 2010-03-31 | FUJIFILM Corporation | Positive-working resist composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2510364A (en) * | 1948-01-16 | 1950-06-06 | Goodrich Co B F | Reaction of beta-lactones with organic magnesium halides |
| GB1198425A (en) * | 1967-06-02 | 1970-07-15 | Bp Chem Int Ltd | Production of Caprolactam |
| US3652596A (en) * | 1967-12-04 | 1972-03-28 | Syntex Corp | Production of unsaturated carbocyclic ketones |
-
1972
- 1972-12-16 DE DE2261751A patent/DE2261751C3/de not_active Expired
-
1973
- 1973-12-07 CA CA187,723A patent/CA1052823A/en not_active Expired
- 1973-12-11 NL NL7316928A patent/NL7316928A/xx not_active Application Discontinuation
- 1973-12-12 CH CH1735773A patent/CH611867A5/xx not_active IP Right Cessation
- 1973-12-13 IT IT2993/73A patent/IT1001411B/it active
- 1973-12-13 US US05/424,308 patent/US3932510A/en not_active Expired - Lifetime
- 1973-12-14 FR FR7344753A patent/FR2210600B1/fr not_active Expired
- 1973-12-14 JP JP48138885A patent/JPS4987649A/ja active Pending
- 1973-12-17 BE BE138955A patent/BE808733A/xx unknown
- 1973-12-17 GB GB5837073A patent/GB1458980A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE808733A (fr) | 1974-06-17 |
| NL7316928A (en:Method) | 1974-06-18 |
| DE2261751A1 (de) | 1974-06-20 |
| DE2261751C3 (de) | 1981-12-24 |
| GB1458980A (en) | 1976-12-22 |
| CH611867A5 (en:Method) | 1979-06-29 |
| DE2261751B2 (de) | 1980-12-04 |
| US3932510A (en) | 1976-01-13 |
| FR2210600A1 (en:Method) | 1974-07-12 |
| JPS4987649A (en:Method) | 1974-08-22 |
| FR2210600B1 (en:Method) | 1977-08-12 |
| IT1001411B (it) | 1976-04-20 |
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