HUT61259A - Process for producing delta-1 enol ethers - Google Patents
Process for producing delta-1 enol ethers Download PDFInfo
- Publication number
- HUT61259A HUT61259A HU9201136A HU9201136A HUT61259A HU T61259 A HUT61259 A HU T61259A HU 9201136 A HU9201136 A HU 9201136A HU 9201136 A HU9201136 A HU 9201136A HU T61259 A HUT61259 A HU T61259A
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- reaction
- acid
- iii
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 150000002084 enol ethers Chemical class 0.000 title description 9
- 108700041286 delta Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 15
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JEPJBZHWRGLINP-UHFFFAOYSA-N 2,2-dimethoxy-3-methylbutane Chemical compound COC(C)(OC)C(C)C JEPJBZHWRGLINP-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl enol ethers Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-N 2,2-diethylpropanedioic acid Chemical compound CCC(CC)(C(O)=O)C(O)=O LTMRRSWNXVJMBA-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006567 deketalization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- IMFKDZCVWYKAAL-UHFFFAOYSA-N phosphoric acid pyridine Chemical compound P(=O)(O)(O)O.N1=CC=CC=C1.N1=CC=CC=C1 IMFKDZCVWYKAAL-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920000642 polymer Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3933247A DE3933247C1 (enrdf_load_stackoverflow) | 1989-10-05 | 1989-10-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU9201136D0 HU9201136D0 (en) | 1992-07-28 |
| HUT61259A true HUT61259A (en) | 1992-12-28 |
Family
ID=6390869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9201136A HUT61259A (en) | 1989-10-05 | 1992-04-03 | Process for producing delta-1 enol ethers |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4433949A1 (de) * | 1994-09-23 | 1996-03-28 | Huels Chemische Werke Ag | Verfahren zur Herstellung von ungesättigten Ethern |
| CN116444352B (zh) * | 2022-01-06 | 2024-06-25 | 万华化学集团股份有限公司 | 一种2-甲氧基丙烯液相合成的新方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE596888A (fr) * | 1959-11-19 | 1961-05-09 | Hoffmann La Roche | Procédé pour la préparation d'éthers énoliques |
| DE3804162A1 (de) * | 1988-02-11 | 1989-08-24 | Basf Ag | Verfahren zur herstellung von vinylethern |
-
1989
- 1989-10-05 DE DE3933247A patent/DE3933247C1/de not_active Expired - Fee Related
-
1990
- 1990-10-01 EP EP90914531A patent/EP0494906A1/de not_active Withdrawn
- 1990-10-01 KR KR1019920700773A patent/KR950006801B1/ko not_active Expired - Lifetime
- 1990-10-01 AU AU64429/90A patent/AU6442990A/en not_active Abandoned
- 1990-10-01 JP JP2513602A patent/JPH05500667A/ja active Pending
- 1990-10-01 WO PCT/EP1990/001646 patent/WO1991004956A1/de not_active Application Discontinuation
- 1990-10-03 IL IL95896A patent/IL95896A0/xx unknown
- 1990-10-04 ZA ZA907922A patent/ZA907922B/xx unknown
-
1992
- 1992-04-03 HU HU9201136A patent/HUT61259A/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA907922B (en) | 1991-07-31 |
| AU6442990A (en) | 1991-04-28 |
| KR950006801B1 (ko) | 1995-06-22 |
| HU9201136D0 (en) | 1992-07-28 |
| WO1991004956A1 (de) | 1991-04-18 |
| KR927003496A (ko) | 1992-12-18 |
| DE3933247C1 (enrdf_load_stackoverflow) | 1991-01-17 |
| IL95896A0 (en) | 1991-07-18 |
| EP0494906A1 (de) | 1992-07-22 |
| JPH05500667A (ja) | 1993-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFA9 | Temporary protection cancelled due to abandonment |