DE1035126B - Process for the preparation of 2-halo-2-methylpentinen-4 - Google Patents
Process for the preparation of 2-halo-2-methylpentinen-4Info
- Publication number
- DE1035126B DE1035126B DEF20611A DEF0020611A DE1035126B DE 1035126 B DE1035126 B DE 1035126B DE F20611 A DEF20611 A DE F20611A DE F0020611 A DEF0020611 A DE F0020611A DE 1035126 B DE1035126 B DE 1035126B
- Authority
- DE
- Germany
- Prior art keywords
- halo
- methylpentinen
- methallylacetylene
- preparation
- carried out
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 2
- OYCKWAPENACEJO-UHFFFAOYSA-N 2-methylpent-1-en-4-yne Chemical group CC(=C)CC#C OYCKWAPENACEJO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 2-Halogen-2-methylpentinen-4 Es wurde gefunden, daß man Halogenwasserstoff an Methallylacetylen anlagern kann, wobei man 2-Halogen-2-methylpentine4 der Formel in der X für Halogen steht, erhält.Process for the preparation of 2-halo-2-methylpentine-4 It has been found that hydrogen halide can be added to methallylacetylene, 2-halo-2-methylpentine-4 of the formula in which X is halogen, is obtained.
Das erfindungsgemäße Verfahren kann sowohl in Gegenwart oder Abwesenheit von Lösungsmitteln durchgeführt werden. Führt man die Reaktion mit organischen Verdünnungsmitteln durch, so setzt man vorteilhafterweise einen Friedel-Crafts-Katalysator, wie z. B. Zinkchlorid, zu, während man bei der Arbeitsweise in wäßrigem Medium keinen Katalysator benötigt. The process according to the invention can be carried out either in the presence or in the absence be carried out by solvents. If the reaction is carried out with organic diluents by, it is advantageous to use a Friedel-Crafts catalyst, such as. B. zinc chloride, while no catalyst when working in an aqueous medium needed.
Das neue Verfahren kann z. B. so durchgeführt werden, daß man bei der Arbeitsweise ohne Lösungsmittel bzw. in einem organischen Lösungsmittel den Halogenwasserstoff einleitet, während er bei der Arbeitsweise in wäßrigem Medium auch in Form einer konzentrierten Lösung zugesetzt werden kann. Die Aufarbeitung der Reaktionsprodukte kann in üblicher Weise vorgenommen werden. The new method can e.g. B. be carried out so that one at the procedure without a solvent or in an organic solvent Introduces hydrogen halide while working in an aqueous medium can also be added in the form of a concentrated solution. The work-up the reaction products can be carried out in a customary manner.
Es war überraschend, daß sich das Methallylacetylen in der beschriebenen Weise umsetzt, ohne daß sich die 3fach-Bindung an der Reaktion beteiligt. Es war weiterhin überraschend, daß das Verfahren in Gegenwart wäßriger konzentrierter Halogenwasserstoffsäuren sogar bei Anwesenheit von Kupfer-l-chlorid durchgeführt werden kann, ohne daß eine nennenswerte Hydratisierung der 3fach-Bindung erfolgt. It was surprising that the methallylacetylene in the described Way, without the triple bond taking part in the reaction. It was further surprising that the process in the presence of aqueous concentrated hydrohalic acids can even be carried out in the presence of copper-l-chloride without a significant hydration of the triple bond occurs.
Die erfindungsgemäß erhaltenen Verbindungen können als Zwischenprodukte für organische Synthesen verwendet werden. The compounds obtained according to the invention can be used as intermediates can be used for organic syntheses.
Beispiel 1 In ein Gemisch von 2 g Zinkchlorid, 25,8 g Methallylacetylen und 60ml Äther wurde 7 Stunden lang bei Raumtemperatur Chlorwasserstoff eingeleitet. Die Destillation lieferte dann 25,6 g 2-Chlor-2-methyl-pentin-4 (Kp.50: 35°C, n200: 1,4352). Ausbeute: 6801o der Theorie. Example 1 In a mixture of 2 g zinc chloride, 25.8 g methallylacetylene and 60 ml of ether was passed in hydrogen chloride for 7 hours at room temperature. The distillation then gave 25.6 g of 2-chloro-2-methyl-pentyne-4 (bp 50: 35 ° C, n200: 1.4352). Yield: 68010 of theory.
Beispiel 2 Ein Gemisch von 39,5 g Methallylacetylen, 100 ml konzentrierter Salzsäure, 0,5 g Kupfer-t-chlorid, 0,3 g Ammoniumchlorid und 0,2 g Kupferpulver wurde bei Raumtemperatur 90 Minuten lang gerührt, dann mit Chlorwasserstoff gesättigt, 2 Stunden weitergerührt und dann aufgearbeitet. Es wurden 46,7 g2-Chlor-2-methyl-pentin-4 erhalten. (Kp.50: 35"C, n200:1,4349). Ausbeute: 81 01o der Theone. Example 2 A mixture of 39.5 g of methallylacetylene, 100 ml more concentrated Hydrochloric acid, 0.5 g copper t-chloride, 0.3 g ammonium chloride and 0.2 g copper powder was stirred at room temperature for 90 minutes, then saturated with hydrogen chloride, Stirred for a further 2 hours and then worked up. There were 46.7 g of 2-chloro-2-methyl-pentin-4 obtain. (Bp 50:35 "C, n200: 1.4349). Yield: 81,010 from Theone.
Beispiel 3 Ein Gemisch von 27,4 g Methallylacetylen und 60 ml konzentrierter Salzsäure wird bei Raumtemperatur 90 Minuten lang gerührt, dann mit Chlorwasserstoff gesättigt, 2 Stunden weitergerührt und dann nach dem Abtrennen der wäßrigen Phase destilliert. Es wurden 33,5 g 2-Chlor-2-methyl-pentin-4 erhalten. Ausbeute: 8401o der Theorie. Example 3 A mixture of 27.4 g of methallylacetylene and 60 ml of concentrated Hydrochloric acid is stirred at room temperature for 90 minutes, then with hydrogen chloride saturated, stirred for a further 2 hours and then after separating off the aqueous phase distilled. 33.5 g of 2-chloro-2-methyl-pentyne-4 were obtained. Yield: 84010 the theory.
Beispiel 4 In ein Gemisch von 16 g Methallylacetylen und 30 ml Äther wurde bei + 30 Bromwasserstoff eingeleitet. Die Destillation des Reaktionsproduktes lieferte 16 g eines Monobromides der Formel (Kp.44: 52°C, n2,0:1,4766) neben höhersiedenden Produkten. Ausbeute: 500/, der Theorie.Example 4 Hydrogen bromide was passed into a mixture of 16 g of methallylacetylene and 30 ml of ether at +30. Distillation of the reaction product yielded 16 g of a monobromide of the formula (Bp 44: 52 ° C, n2.0: 1.4766) next to higher-boiling products. Yield: 500 /, the theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20611A DE1035126B (en) | 1956-06-25 | 1956-06-25 | Process for the preparation of 2-halo-2-methylpentinen-4 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20611A DE1035126B (en) | 1956-06-25 | 1956-06-25 | Process for the preparation of 2-halo-2-methylpentinen-4 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1035126B true DE1035126B (en) | 1958-07-31 |
Family
ID=7089742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF20611A Pending DE1035126B (en) | 1956-06-25 | 1956-06-25 | Process for the preparation of 2-halo-2-methylpentinen-4 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1035126B (en) |
-
1956
- 1956-06-25 DE DEF20611A patent/DE1035126B/en active Pending
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