DE2557011A1 - Verfahren zur herstellung von alpha- arylsubstituierten propionsaeurealkylestern - Google Patents
Verfahren zur herstellung von alpha- arylsubstituierten propionsaeurealkylesternInfo
- Publication number
- DE2557011A1 DE2557011A1 DE19752557011 DE2557011A DE2557011A1 DE 2557011 A1 DE2557011 A1 DE 2557011A1 DE 19752557011 DE19752557011 DE 19752557011 DE 2557011 A DE2557011 A DE 2557011A DE 2557011 A1 DE2557011 A1 DE 2557011A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- propionic acid
- aryl
- ata
- general formula
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 21
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 235000019260 propionic acid Nutrition 0.000 title claims description 7
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class 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 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 150000002366 halogen compounds Chemical class 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 3
- 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 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001649 bromium compounds Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 125000000075 primary alcohol group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- -1 alcohol ions Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 2
- PLKSMSKTENNPEJ-UHFFFAOYSA-N 1-methoxyethylbenzene Chemical compound COC(C)C1=CC=CC=C1 PLKSMSKTENNPEJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000003151 propanoic acid esters Chemical class 0.000 description 2
- 150000004672 propanoic acids Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- SPBVCQUMYJRBMD-UHFFFAOYSA-N 1-(1-chloroethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C(C)Cl)C=C1 SPBVCQUMYJRBMD-UHFFFAOYSA-N 0.000 description 1
- MVTKJCAAJPVUHJ-UHFFFAOYSA-N 1-ethoxyethylbenzene Chemical compound CCOC(C)C1=CC=CC=C1 MVTKJCAAJPVUHJ-UHFFFAOYSA-N 0.000 description 1
- DYNVRFFVBZVRND-UHFFFAOYSA-N 3-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(CCC(O)=O)C=C1 DYNVRFFVBZVRND-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000009835 boiling Methods 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- OBTSLRFPKIKXSZ-UHFFFAOYSA-N lithium potassium Chemical compound [Li].[K] OBTSLRFPKIKXSZ-UHFFFAOYSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- DZIQUZJSNSZOCH-UHFFFAOYSA-N methyl 2-phenylpropanoate Chemical compound COC(=O)C(C)C1=CC=CC=C1 DZIQUZJSNSZOCH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752557011 DE2557011A1 (de) | 1975-12-18 | 1975-12-18 | Verfahren zur herstellung von alpha- arylsubstituierten propionsaeurealkylestern |
| GB5221776A GB1560082A (en) | 1975-12-18 | 1976-12-14 | Process for producing an x-aryl-substituted propionic acid alkyl ester |
| BE173312A BE849467A (fr) | 1975-12-18 | 1976-12-16 | Procede de preparation d'esters alkyliques d'acide propionique alpha -arylsubstitues |
| IT5265276A IT1074222B (it) | 1975-12-18 | 1976-12-16 | Procedimento per la produzione di propionati alchilici alfa/aril sostituiti |
| FR7638239A FR2335489A1 (fr) | 1975-12-18 | 1976-12-17 | Procede de preparation d'esters alkyliques d'acide propionique a-arylsubstitues |
| JP15187476A JPS5277029A (en) | 1975-12-18 | 1976-12-17 | Production of alphaa aryl substituted propionic acid alkylester |
| NL7614045A NL7614045A (nl) | 1975-12-18 | 1976-12-17 | Werkwijze voor het bereiden van (alpha)-aryl-gesub- stitueerde propionzuuralkylesters. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752557011 DE2557011A1 (de) | 1975-12-18 | 1975-12-18 | Verfahren zur herstellung von alpha- arylsubstituierten propionsaeurealkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2557011A1 true DE2557011A1 (de) | 1977-06-23 |
Family
ID=5964712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752557011 Ceased DE2557011A1 (de) | 1975-12-18 | 1975-12-18 | Verfahren zur herstellung von alpha- arylsubstituierten propionsaeurealkylestern |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5277029A (enExample) |
| BE (1) | BE849467A (enExample) |
| DE (1) | DE2557011A1 (enExample) |
| FR (1) | FR2335489A1 (enExample) |
| GB (1) | GB1560082A (enExample) |
| IT (1) | IT1074222B (enExample) |
| NL (1) | NL7614045A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0326027A1 (de) * | 1988-01-29 | 1989-08-02 | Hoechst Aktiengesellschaft | Verfahren zur Reinigung von 2-(4-Isobutylphenyl)-propionsäure |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001288A (en) * | 1988-08-26 | 1991-03-19 | Ethyl Corporation | Haloethylation of aromatic hydrocarbons |
| CA2000958A1 (en) * | 1988-11-14 | 1990-05-14 | Barbara C. Stahly | Haloalkylation of aromatic compounds |
| US5319150A (en) * | 1988-11-14 | 1994-06-07 | Albemarle Corporation | Chloroalkylation of aromatic compounds |
-
1975
- 1975-12-18 DE DE19752557011 patent/DE2557011A1/de not_active Ceased
-
1976
- 1976-12-14 GB GB5221776A patent/GB1560082A/en not_active Expired
- 1976-12-16 BE BE173312A patent/BE849467A/xx unknown
- 1976-12-16 IT IT5265276A patent/IT1074222B/it active
- 1976-12-17 JP JP15187476A patent/JPS5277029A/ja active Pending
- 1976-12-17 NL NL7614045A patent/NL7614045A/xx not_active Application Discontinuation
- 1976-12-17 FR FR7638239A patent/FR2335489A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0326027A1 (de) * | 1988-01-29 | 1989-08-02 | Hoechst Aktiengesellschaft | Verfahren zur Reinigung von 2-(4-Isobutylphenyl)-propionsäure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5277029A (en) | 1977-06-29 |
| FR2335489B1 (enExample) | 1980-11-07 |
| GB1560082A (en) | 1980-01-30 |
| BE849467A (fr) | 1977-04-15 |
| NL7614045A (nl) | 1977-06-21 |
| IT1074222B (it) | 1985-04-17 |
| FR2335489A1 (fr) | 1977-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |