BE719104A - - Google Patents
Info
- Publication number
- BE719104A BE719104A BE719104DA BE719104A BE 719104 A BE719104 A BE 719104A BE 719104D A BE719104D A BE 719104DA BE 719104 A BE719104 A BE 719104A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- copper
- reaction
- copper powder
- mixture
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000017105 transposition Effects 0.000 description 3
- ZIVBFCKAZCKNIS-UHFFFAOYSA-N 2-hydroxy-2-methylbut-3-enal Chemical compound C=CC(O)(C)C=O ZIVBFCKAZCKNIS-UHFFFAOYSA-N 0.000 description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-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
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 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
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- -1 hydrochloric acids Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB93850A DE1297597B (de) | 1967-08-08 | 1967-08-08 | Verfahren zur Herstellung von Carbonsaeureestern des ª‰-Formylcrothylalkohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE719104A true BE719104A (d) | 1969-02-06 |
Family
ID=6987197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE719104D BE719104A (d) | 1967-08-08 | 1968-08-06 |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE719104A (d) |
| DE (1) | DE1297597B (d) |
| NL (1) | NL6810954A (d) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840125A1 (de) * | 1978-09-15 | 1980-04-03 | Basf Ag | Verfahren zur herstellung von carbonsaeureestern des beta -formyl-crotylalkohols mittels einer allylumlagerung |
| US4301084A (en) | 1979-08-31 | 1981-11-17 | Basf Aktiengesellschaft | Process for the preparation of carboxylic acid esters of β-formyl-crotyl alcohol by an allyl rearrangement |
| DE3639562A1 (de) * | 1986-11-20 | 1988-06-01 | Basf Ag | Verfahren zur herstellung von 2-substituierten 4-acyloxi-2-butenalen |
-
1967
- 1967-08-08 DE DEB93850A patent/DE1297597B/de active Pending
-
1968
- 1968-08-01 NL NL6810954A patent/NL6810954A/xx unknown
- 1968-08-06 BE BE719104D patent/BE719104A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6810954A (d) | 1969-02-11 |
| DE1297597B (de) | 1969-06-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2533920C2 (de) | Verfahren zur Herstellung von Resorcinen | |
| CH627149A5 (en) | Process for the preparation of lower alkyl esters of racemic cis- or trans-3-formyl-2,2-disubstituted-1-cyclopropanecarboxylic acids | |
| BE719104A (d) | ||
| FR2596755A1 (fr) | Procede de preparation de composes carbonyles ethyleniques | |
| JP2002524435A (ja) | キャロル反応によるγ、δ−不飽和ケトンの製造方法 | |
| DE3125891A1 (de) | Verfahren zur herstellung von 2-alkyl-4,4-diacyloxy-2-butenalen | |
| US4301084A (en) | Process for the preparation of carboxylic acid esters of β-formyl-crotyl alcohol by an allyl rearrangement | |
| BRPI0706550A2 (pt) | processos para produzir bisabolol e para produzir ésteres de farnesol | |
| DE2103686B2 (de) | Verfahren zur Herstellung von a -Hydroxy- γ -lactonen | |
| US3639437A (en) | Production of carboxylic esters of beth-formylcrotyl alcohol | |
| US4918052A (en) | Perfume base composition | |
| DE2918901A1 (de) | 1,5-dimethyl-bicyclo eckige klammer auf 3,2,1 eckige klammer zu octan-derivate, verfahren zu ihrer herstellung und ihre verwendung | |
| US3118930A (en) | Process for the preparation of gamma-oxosenecioic acid esters | |
| FR2549041A1 (fr) | Procede de purification de 4-fluorophenol | |
| US2698341A (en) | Acidolysis of methylal with carboxylic acid anhydroides | |
| EP0735032B1 (de) | Verfahren zur Herstellung von 5-Hydroxy-4-methyl-2(5H)-furanon | |
| EP0087097B1 (de) | 2-Alkyl-1,3-diacyloxy-4-hydroxy-1-butene, ihre Herstellung und Verwendung | |
| FR2486935A1 (fr) | Traitement d'esters de diacide par des hydroborates, permanganates ou methoxydes alcalins | |
| JPS61204152A (ja) | アシロキシナフタレンおよびその誘導体の製造法 | |
| FR2500442A1 (fr) | Procede pour la preparation d'un acide chrysanthemique d'une haute purete | |
| BE653303A (d) | ||
| JPS6127372B2 (d) | ||
| CH398565A (fr) | Procédé de préparation de l'acide cyclododécane-carboxylique | |
| JPS5855128B2 (ja) | ポリプレニルカゴウブツ ノ セイホウ | |
| CH500964A (de) | Verfahren zur Herstellung von 2,3-Dihydro-2,2,4-trimethyl-7-benzofuranol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE20 | Patent expired |
Owner name: BADISCHE ANILIN- & SODAFABRIK A.G. Effective date: 19880806 |