DD229126A5 - Verfahren zur herstellung von tetronsaeure - Google Patents
Verfahren zur herstellung von tetronsaeure Download PDFInfo
- Publication number
- DD229126A5 DD229126A5 DD85272648A DD27264885A DD229126A5 DD 229126 A5 DD229126 A5 DD 229126A5 DD 85272648 A DD85272648 A DD 85272648A DD 27264885 A DD27264885 A DD 27264885A DD 229126 A5 DD229126 A5 DD 229126A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acid
- hydrogenation
- tetronic acid
- converted
- tetronic
- Prior art date
Links
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 title claims abstract description 25
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- DJEJYZZJYYNADA-UHFFFAOYSA-N 3-chlorooxolane-2,4-dione Chemical compound ClC1C(=O)COC1=O DJEJYZZJYYNADA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 238000007669 thermal treatment Methods 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000008262 pumice Substances 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 16
- 150000002148 esters Chemical class 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- -1 i.a. Toluene Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GPDFVBIDCBPHSW-UHFFFAOYSA-N ethyl 2,4-dichloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(=O)CCl GPDFVBIDCBPHSW-UHFFFAOYSA-N 0.000 description 1
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002506 high-vacuum sublimation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- HFLMYYLFSNEOOT-UHFFFAOYSA-N methyl 4-chloro-3-oxobutanoate Chemical compound COC(=O)CC(=O)CCl HFLMYYLFSNEOOT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH604/84A CH658056A5 (de) | 1984-02-09 | 1984-02-09 | Verfahren zur herstellung von tetronsaeure. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD229126A5 true DD229126A5 (de) | 1985-10-30 |
Family
ID=4190834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85272648A DD229126A5 (de) | 1984-02-09 | 1985-01-18 | Verfahren zur herstellung von tetronsaeure |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0153615B1 (en, 2012) |
| JP (1) | JPS60184073A (en, 2012) |
| AT (1) | ATE42550T1 (en, 2012) |
| CA (1) | CA1225094A (en, 2012) |
| CH (1) | CH658056A5 (en, 2012) |
| DD (1) | DD229126A5 (en, 2012) |
| DE (1) | DE3569735D1 (en, 2012) |
| HU (1) | HU196066B (en, 2012) |
| IL (1) | IL74131A (en, 2012) |
| IN (1) | IN162567B (en, 2012) |
| MX (1) | MX156171A (en, 2012) |
| SU (1) | SU1436868A3 (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63112883U (en, 2012) * | 1987-01-13 | 1988-07-20 | ||
| CA2211503A1 (en) * | 1996-09-04 | 1998-03-04 | Josef Schroer | Process for the preparation of tetronic acid derivatives |
| CA2210821A1 (en) * | 1996-09-04 | 1998-03-04 | Lonza Ag | Process for the preparation of an arylazotetronic acid derivative |
| AUPQ841900A0 (en) * | 2000-06-28 | 2000-07-20 | Unisearch Limited | Synthesis of cyclic compounds |
| EP2039678A1 (de) | 2007-09-18 | 2009-03-25 | Bayer CropScience AG | Verfahren zum Herstellen von 4-Aminobut-2-enoliden |
| EP2042496A1 (de) | 2007-09-18 | 2009-04-01 | Bayer CropScience AG | Verfahren zur Herstellung von 4-Aminobut-2-enoliden |
| JP2010070460A (ja) | 2008-09-16 | 2010-04-02 | Daicel Chem Ind Ltd | テトロン酸の製造方法 |
| EP2230237A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
| EP2230236A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
| TW201111370A (en) | 2009-08-18 | 2011-04-01 | Bayer Cropscience Ag | Novel process for the preparation of 4-aminobut-2-enolides |
| KR101721222B1 (ko) | 2009-12-23 | 2017-03-29 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 4-알콕시푸란-2(5ｈ)-온 또는 4-아릴알콕시푸란-2(5ｈ)-온으로부터 4-아미노부트-2-에놀라이드의 신규 제조방법 |
| CN106632081A (zh) * | 2016-12-14 | 2017-05-10 | 四川同晟生物医药有限公司 | 一种5‑氯‑6‑(氯甲基)尿嘧啶及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH529128A (de) * | 1970-09-04 | 1972-10-15 | Lonza Ag | Verfahren zur Herstellung von Tetronsäure |
| CH649294A5 (de) * | 1981-06-17 | 1985-05-15 | Lonza Ag | Verfahren zur herstellung von tetronsaeure. |
| CH649996A5 (de) * | 1981-06-17 | 1985-06-28 | Lonza Ag | Verfahren zur herstellung von tetronsaeure. |
-
1984
- 1984-02-09 CH CH604/84A patent/CH658056A5/de not_active IP Right Cessation
-
1985
- 1985-01-14 HU HU85132A patent/HU196066B/hu not_active IP Right Cessation
- 1985-01-18 DD DD85272648A patent/DD229126A5/de not_active IP Right Cessation
- 1985-01-22 IL IL74131A patent/IL74131A/xx unknown
- 1985-01-22 IN IN52/MAS/85A patent/IN162567B/en unknown
- 1985-02-04 DE DE8585101150T patent/DE3569735D1/de not_active Expired
- 1985-02-04 EP EP85101150A patent/EP0153615B1/de not_active Expired
- 1985-02-04 AT AT85101150T patent/ATE42550T1/de not_active IP Right Cessation
- 1985-02-06 MX MX204247A patent/MX156171A/es unknown
- 1985-02-07 CA CA000473780A patent/CA1225094A/en not_active Expired
- 1985-02-08 SU SU853853848A patent/SU1436868A3/ru active
- 1985-02-08 JP JP60023386A patent/JPS60184073A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3569735D1 (en) | 1989-06-01 |
| JPS6156232B2 (en, 2012) | 1986-12-01 |
| HUT39441A (en) | 1986-09-29 |
| IL74131A0 (en) | 1985-04-30 |
| HU196066B (en) | 1988-09-28 |
| JPS60184073A (ja) | 1985-09-19 |
| IN162567B (en, 2012) | 1988-06-11 |
| ATE42550T1 (de) | 1989-05-15 |
| MX156171A (es) | 1988-07-19 |
| EP0153615A1 (de) | 1985-09-04 |
| IL74131A (en) | 1988-11-30 |
| EP0153615B1 (de) | 1989-04-26 |
| CH658056A5 (de) | 1986-10-15 |
| CA1225094A (en) | 1987-08-04 |
| SU1436868A3 (ru) | 1988-11-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2721264C2 (de) | Verfahren zur Herstellung von Di-n-propylessigsäure und deren nichttoxischen Alkali- und Erdalkalimetallsalzen | |
| DD229126A5 (de) | Verfahren zur herstellung von tetronsaeure | |
| EP0847990A1 (de) | 4-(C1-C4)-Alkoxy-3-pyrrolin-2-on-1-yl-essigsäuren, deren Herstellung und Verwendung zur Synthese von 4-Hydroxy-2-oxo-pyrrolidin-1-yl-acetamid | |
| DE2714081C2 (de) | Verfahren zur Herstellung von 2-(2,2-Dicyclohexylethyl)-piperidin | |
| DE2806909C2 (en, 2012) | ||
| DE2461307C3 (de) | 2-Hydroxymethy!-3-hydroxypyridin-6-epoxyäthan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 2-Hydroxymethyl-3hydroxy-6-( 1 -hydrOxy-2-tert.butylaminoäthyDpyridin | |
| DE2721265C2 (de) | Verfahren zur Herstellung von Di- n-propylacetonitril | |
| DE2834312C2 (de) | Verfahren zur Herstellung von 2[N-(2-Hydroxyäthyl)-N-niederalkylaminomethyl]-benzhydrolen | |
| DE3203487A1 (de) | Verfahren zur herstellung von tocopherylacetat oder tocopherylpropionat | |
| DD210034A5 (de) | Verfahren zur herstellung von pirbuterol | |
| DE2166997C3 (de) | Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen | |
| DE2034682A1 (de) | Herstellung von eis 1 Propenylphos phonsaure | |
| DE68906563T2 (de) | 2(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinon.Verfahren zur Herstellung und Verfahren zur Herstellung daraus von 2-(1-alkenyl)-3-hydroxy-1,4-naphthochinon und 2-alkyl-3-acyloxy-1,4 naphthochinon. | |
| EP0056615B1 (de) | Verfahren zur Herstellung von Carnitinamid | |
| EP0423595B1 (de) | Verfahren zur Herstellung von 3-Trichlormethyl-pyridin | |
| DE2331665A1 (de) | Dialkylaminoalkylester von arylaliphatischen saeuren und ihre saeureadditionssalze und verfahren zu deren herstellung | |
| CH652388A5 (de) | Verfahren zur herstellung von propafenon. | |
| DE2618721C2 (de) | Benzo(b)-bicyclo[3,3,1]nonene, Verfahren zu deren Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten | |
| DE2139084B2 (de) | Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| DE1620658C (de) | l-Phenyl-4-aminopyrazolderivate und Verfahren zu ihrer Herstellung | |
| DE2833967A1 (de) | Verfahren zur herstellung von apovincamin | |
| DE2735569C2 (en, 2012) | ||
| AT333981B (de) | Verfahren zur herstellung des neuen n-(d-6-methyl-8-isoergolin-i-yl)-n',n'-diathylharnstoffs | |
| DE1445427C (de) | 1,1 Diphenyl 2 (2 piperidinyl) pro pionsaureathylester, dessen Saureadditions salze und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |