JPS6159298B2 - - Google Patents
Info
- Publication number
- JPS6159298B2 JPS6159298B2 JP53056720A JP5672078A JPS6159298B2 JP S6159298 B2 JPS6159298 B2 JP S6159298B2 JP 53056720 A JP53056720 A JP 53056720A JP 5672078 A JP5672078 A JP 5672078A JP S6159298 B2 JPS6159298 B2 JP S6159298B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methyl
- oxoacetal
- ethyl
- ethylene type
- 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
- 239000005977 Ethylene Substances 0.000 claims description 16
- -1 orthoformic acid ester Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- TXBMCLDHFRIQLA-UHFFFAOYSA-N trimethyl(3-methylbuta-1,3-dienoxy)silane Chemical compound CC(=C)C=CO[Si](C)(C)C TXBMCLDHFRIQLA-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- AIUVIHYATZICHW-UHFFFAOYSA-N 5,5-diethoxy-3-methylpent-3-en-2-one Chemical compound CCOC(OCC)C=C(C)C(C)=O AIUVIHYATZICHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002905 orthoesters Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons 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
- 229910052796 boron Inorganic materials 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
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- FGCLOJOLJQDQOG-UHFFFAOYSA-N ethoxymethanediol Chemical class CCOC(O)O FGCLOJOLJQDQOG-UHFFFAOYSA-N 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- UDECNVKNELCBHM-UHFFFAOYSA-N trimethyl(3-methylidenepent-1-enoxy)silane Chemical compound C(C)C(C=CO[Si](C)(C)C)=C UDECNVKNELCBHM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7715070A FR2391181A1 (fr) | 1977-05-17 | 1977-05-17 | Procede de preparation de d-oxoacetals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53141204A JPS53141204A (en) | 1978-12-08 |
| JPS6159298B2 true JPS6159298B2 (fr) | 1986-12-16 |
Family
ID=9190911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5672078A Granted JPS53141204A (en) | 1977-05-17 | 1978-05-15 | Process for preparing deltaaoxoacetal |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS53141204A (fr) |
| BE (1) | BE867127A (fr) |
| CA (1) | CA1108646A (fr) |
| CH (1) | CH633246A5 (fr) |
| DD (1) | DD135481A5 (fr) |
| DE (1) | DE2821540A1 (fr) |
| FR (1) | FR2391181A1 (fr) |
| GB (1) | GB1591968A (fr) |
| HU (1) | HU179295B (fr) |
| IT (1) | IT1096298B (fr) |
| NL (1) | NL188634C (fr) |
| SU (1) | SU869553A3 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2654105B1 (fr) * | 1989-11-09 | 1992-02-21 | Univ Rouen | Nouveaux dienoxysilanes, leur procede d'obtention, et nouveaux aldehydes alpha-ethyleniques alpha-halogenes auxquels ils donnent acces. |
-
1977
- 1977-05-17 FR FR7715070A patent/FR2391181A1/fr active Granted
-
1978
- 1978-05-09 NL NLAANVRAGE7804965,A patent/NL188634C/xx not_active IP Right Cessation
- 1978-05-15 JP JP5672078A patent/JPS53141204A/ja active Granted
- 1978-05-15 GB GB19655/78A patent/GB1591968A/en not_active Expired
- 1978-05-16 BE BE187743A patent/BE867127A/fr not_active IP Right Cessation
- 1978-05-16 CH CH529178A patent/CH633246A5/fr not_active IP Right Cessation
- 1978-05-16 DD DD78205394A patent/DD135481A5/xx unknown
- 1978-05-16 HU HU78RO980A patent/HU179295B/hu not_active IP Right Cessation
- 1978-05-16 CA CA303,499A patent/CA1108646A/fr not_active Expired
- 1978-05-17 DE DE19782821540 patent/DE2821540A1/de active Granted
- 1978-05-17 SU SU782615802A patent/SU869553A3/ru active
- 1978-05-17 IT IT23510/78A patent/IT1096298B/it active
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS=1967 * |
| CHEMICAL ABSTRACTS=1973 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1108646A (fr) | 1981-09-08 |
| CH633246A5 (en) | 1982-11-30 |
| DE2821540A1 (de) | 1978-11-23 |
| IT7823510A0 (it) | 1978-05-17 |
| JPS53141204A (en) | 1978-12-08 |
| BE867127A (fr) | 1978-11-16 |
| DD135481A5 (de) | 1979-05-09 |
| SU869553A3 (ru) | 1981-09-30 |
| FR2391181A1 (fr) | 1978-12-15 |
| NL188634B (nl) | 1992-03-16 |
| DE2821540C2 (fr) | 1988-02-18 |
| IT1096298B (it) | 1985-08-26 |
| NL188634C (nl) | 1992-08-17 |
| NL7804965A (nl) | 1978-11-21 |
| FR2391181B1 (fr) | 1981-01-09 |
| GB1591968A (en) | 1981-07-01 |
| HU179295B (en) | 1982-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0186117A2 (fr) | Procédé de préparation de composés dicétoniques acylés | |
| KR870002015B1 (ko) | 2,2-디플루오로프로피온산 유도체의 제조방법 | |
| Olah et al. | Synthetic methods and reactions. 123. Preparation of. alpha.-chloro ketones from enol silyl ethers with sulfuryl chloride fluoride and sulfuryl chloride | |
| EP0847974A1 (fr) | Procédé de préparation de cyclopropylacétylène et de ses dérivés | |
| RU2065849C1 (ru) | Способ получения 2-гидроксибензальдегида | |
| JPS6159298B2 (fr) | ||
| JP3579437B2 (ja) | ２−ヒドロキシアリールアルデヒドの製法 | |
| KR100724594B1 (ko) | 1-아세톡시-3-(3,4-c1 또는 c2알킬렌디옥시페닐) 프로펜 화합물 | |
| US5457238A (en) | Process for the preparation of fluoroketones | |
| CN108164403B (zh) | 7-甲基-3-亚甲基-7-辛烯醛缩醛化合物以及用其生产醛类和酯类化合物的方法 | |
| Bellassoued et al. | Two-carbon homologation of ketones via sily ketene acetals: Synthesis of α, β-unsaturated acids and α-trimethylsilyl δ-ketoacids | |
| JPH06206835A (ja) | ハロゲン化芳香族化合物の製造法 | |
| US6063940A (en) | Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof | |
| EP3464235B1 (fr) | Procédé de préparation de composés de type polysantol | |
| JPS6210497B2 (fr) | ||
| JP4008306B2 (ja) | 末端アルキンの製造法 | |
| JPH10101614A (ja) | α，α−ジフルオロ−β−ヒドロキシエステルの製造方法 | |
| Davin et al. | A large scale preparation of 1-ethynylcyclopentene and 1-hexen-4-yne | |
| Tanabe | Carbon Homologation of 1-Alkynes Using Alkoxymethyl Esters Mediated by Dichlorobis (trifluoromethanesulfonato) titanium (IV). | |
| JPS6148815B2 (fr) | ||
| HU199485B (en) | Process for production of derivatives of /aril/-/dimethil/-/3-(4-fluor-3-ariloxi-phenil)-prophil/-silane | |
| JP4800933B2 (ja) | シクロプロパンモノアセタール誘導体の製造方法およびその中間体 | |
| JPH045671B2 (fr) | ||
| JPS6157318B2 (fr) | ||
| CA2157315A1 (fr) | Procede pour la preparation de fluorocetones |