GB1560082A - Process for producing an x-aryl-substituted propionic acid alkyl ester - Google Patents
Process for producing an x-aryl-substituted propionic acid alkyl ester Download PDFInfo
- Publication number
- GB1560082A GB1560082A GB5221776A GB5221776A GB1560082A GB 1560082 A GB1560082 A GB 1560082A GB 5221776 A GB5221776 A GB 5221776A GB 5221776 A GB5221776 A GB 5221776A GB 1560082 A GB1560082 A GB 1560082A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- yield
- ester
- acid methyl
- methyl ester
- 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 description 48
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 24
- 235000019260 propionic acid Nutrition 0.000 title claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- -1 hydratropic acid methyl ester Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000002366 halogen compounds Chemical class 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 239000007832 Na2SO4 Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000012259 ether extract Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229910052744 lithium Chemical group 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 101000931682 Homo sapiens Protein furry homolog-like Proteins 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 102100020916 Protein furry homolog-like Human genes 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 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 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 229960003750 ethyl chloride Drugs 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910021012 Co2(CO)8 Inorganic materials 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002927 oxygen compounds Chemical class 0.000 description 2
- 150000004672 propanoic acids Chemical class 0.000 description 2
- 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 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229910003251 Na K Inorganic materials 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical class CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 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)
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 |
|---|---|
| GB1560082A true GB1560082A (en) | 1980-01-30 |
Family
ID=5964712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5221776A Expired GB1560082A (en) | 1975-12-18 | 1976-12-14 | Process for producing an x-aryl-substituted propionic acid alkyl ester |
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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001288A (en) * | 1988-08-26 | 1991-03-19 | Ethyl Corporation | Haloethylation of aromatic hydrocarbons |
| US5136115A (en) * | 1988-11-14 | 1992-08-04 | Stahly Barbara C | Bromoalkylation of aromatic compounds |
| US5319150A (en) * | 1988-11-14 | 1994-06-07 | Albemarle Corporation | Chloroalkylation of aromatic compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3802619C1 (enExample) * | 1988-01-29 | 1989-09-07 | Hoechst Ag, 6230 Frankfurt, De |
-
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 IT IT5265276A patent/IT1074222B/it active
- 1976-12-16 BE BE173312A patent/BE849467A/xx unknown
- 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001288A (en) * | 1988-08-26 | 1991-03-19 | Ethyl Corporation | Haloethylation of aromatic hydrocarbons |
| US5136115A (en) * | 1988-11-14 | 1992-08-04 | Stahly Barbara C | Bromoalkylation of aromatic compounds |
| US5319150A (en) * | 1988-11-14 | 1994-06-07 | Albemarle Corporation | Chloroalkylation of aromatic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1074222B (it) | 1985-04-17 |
| JPS5277029A (en) | 1977-06-29 |
| FR2335489B1 (enExample) | 1980-11-07 |
| BE849467A (fr) | 1977-04-15 |
| DE2557011A1 (de) | 1977-06-23 |
| FR2335489A1 (fr) | 1977-07-15 |
| NL7614045A (nl) | 1977-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4443624A (en) | Method of preparing malonic acid dialkyl esters | |
| JPH05112492A (ja) | 脂肪族カルボン酸ハロメチルエステル類の製造法 | |
| US3356734A (en) | Process for the production of acetaldehyde | |
| US4434297A (en) | Process for the preparation of trifluoroethanol | |
| GB1560082A (en) | Process for producing an x-aryl-substituted propionic acid alkyl ester | |
| JPS6137268B2 (enExample) | ||
| JP2693615B2 (ja) | １‐ハロ‐４，６，１０‐ヘキサデカトリエン化合物およびその製造方法 | |
| JPS6210978B2 (enExample) | ||
| JPH0662488B2 (ja) | バルプロ酸の製造方法 | |
| US3631067A (en) | Preparation of coumarin | |
| US1926059A (en) | Oxidation of secondary alcohols | |
| JPH0129783B2 (enExample) | ||
| US2124851A (en) | Halogen-substituted alcohols and a process of preparing them | |
| US3957838A (en) | Process for production of fatty acid salt and ester thereof by alkaline fusion oxidation reaction | |
| US5773641A (en) | Synthesis of esters of mercaptocarboxylic acids | |
| US2984688A (en) | Methods for producing vinyl ethers | |
| JP3386596B2 (ja) | ５（ｅ），８（ｚ），１１（ｚ）−テトラデカトリエン−２−オンの製造方法 | |
| US4492798A (en) | Process for preparing arylalkylpyruvic acids | |
| US2832803A (en) | Manufacture of trichloroacetic acid | |
| US3578703A (en) | Process for producing methyl formate from alkali or alkaline earth formate | |
| US2162676A (en) | Preparation of acetylene glycols | |
| CN1288454A (zh) | 由3,4－环氧－1－丁烯制备3－丁烯－1－醇 | |
| US3993703A (en) | Preparation of 2-hydrocarbylglycerols | |
| US4738802A (en) | Process for preparing alkyl α-keto-carboxylic acids from alkyl halides | |
| KR100524257B1 (ko) | 테프레논의 실용적인 합성 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |