DE2305235A1 - NEW ISOPRENIC SULPHONES - Google Patents
NEW ISOPRENIC SULPHONESInfo
- Publication number
- DE2305235A1 DE2305235A1 DE19732305235 DE2305235A DE2305235A1 DE 2305235 A1 DE2305235 A1 DE 2305235A1 DE 19732305235 DE19732305235 DE 19732305235 DE 2305235 A DE2305235 A DE 2305235A DE 2305235 A1 DE2305235 A1 DE 2305235A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- sulfones
- halogen atom
- sulphones
- new
- 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
- 150000003457 sulfones Chemical class 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 2
- 102100033227 Teneurin-2 Human genes 0.000 claims 1
- 101710122316 Teneurin-2 Proteins 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- -1 alkenyl radical Chemical class 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VDLWSAISTMYDDE-UHFFFAOYSA-N 2-chlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=CC=C1Cl VDLWSAISTMYDDE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SAVZPUKLCRAJFP-UHFFFAOYSA-N CC(CCl)C(S(C(C(C)CCl)=CC1=CC=CC=C1)(=O)=O)=CC1=CC=CC=C1 Chemical compound CC(CCl)C(S(C(C(C)CCl)=CC1=CC=CC=C1)(=O)=O)=CC1=CC=CC=C1 SAVZPUKLCRAJFP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 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 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/08—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PATENTANWÄLTEPATENT LAWYERS
BANKKONTO: BANKHAUS H. AUFHÄUSERBANK ACCOUNT: BANK H. HOUSES
8 MÜNCHEN 2.8 MUNICH 2.
SC 4028/4055SC 4028/4055
EHOKE-POULEFC S.A., Paris/Frankrei chEHOKE-POULEFC S.A., Paris / France
Neue Isoprenische SulfoneNew isoprenic sulfones
Die vorliegende Erfindung betrifft neue Sulfone der allgemeinen FormelThe present invention relates to new sulfones of the general formula
X-CH2- C(CH3) = CH - CH2SO2R IX-CH 2 - C (CH 3) = CH - CH 2 SO 2 RI
in der X .ein Halogenatom, vorzugsweise Chlor oder Brom, oder eine Gruppe -SO R bedeutet. R bedeutet einen Alkyl-, Alkenyl-, Aralkyl-, Alkylaryl- oder Arylrest, wobei jeder dieser Reste gegebenenfalls durch Elektronen anziehende oder Elektronen liefernde Gruppen substituiert sein kann.in the X. a halogen atom, preferably chlorine or bromine, or a group -SO R means. R denotes an alkyl, alkenyl, aralkyl, alkylaryl or aryl radical, each of these radicals may optionally be substituted by electron attracting or electron donating groups.
Im besonderen umfaßt der Rest R insgesamt höchstens 15 Kohlenstoff atome, wenn es sich um einen Alkyl- oder Alkenylrest handelt und 6 bis 18 Kohlenstoffatome, wenn es sich um einen Aralkyl-, Alkylaryl- oder Arylrest handelt. Die Substituenten für R können insbesondere folgende Gruppen sein: Nitro, Amino, Cyano, Acyl, Formyl, Carboxyl, Carboxylat, Alkoxy, Alkylthio, Alkylsulfinyl und Alkyl-sulfonyl.In particular, the radical R comprises a total of at most 15 carbon atoms, if it is an alkyl or alkenyl radical and 6 to 18 carbon atoms, if it is an aralkyl, Alkylaryl or aryl radical is. The substituents for R can in particular be the following groups: nitro, amino, cyano, acyl, Formyl, carboxyl, carboxylate, alkoxy, alkylthio, alkylsulfinyl and alkyl-sulfonyl.
Insbesondere kann man als Reste R die folgenden nennen: DenIn particular, the following can be mentioned as radicals R: Den
309833/1139309833/1139
Allyl-, 3-Methylbuten-2~yl-, den 3-Methylbutadien-1,3-yl-, den Isopropenyl-, Geranyl-, Farnesyl-, Methyl-, lthyl-, Isopropyl-, tert.-Butyl-, Hexyl-, Dodecyl-, Phenyl-, Naphthyl-, Anthracenyl-Tolyl-, Xylyl-, Benzyl-, Phenyläthyl- und Triphenylmethylrest.Allyl, 3-methylbuten-2 ~ yl, 3-methylbutadien-1,3-yl, the Isopropenyl, geranyl, farnesyl, methyl, ethyl, isopropyl, tert-butyl, hexyl, dodecyl, phenyl, naphthyl, anthracenyl-tolyl, Xylyl, benzyl, phenylethyl and triphenylmethyl radical.
Diese neuen Sulfone können aufgrund ihrer Reaktivität, die ihnen-ihre SuIfon- und Haiοgengruppen verleihen, "bei verschiedenen organischen Synthesen verwendet werden.These new sulfones can because of their reactivity, which give them-their sulfone and shark groups, "in different organic syntheses are used.
In' verschiedenen Publikationen (französische Patentschrift 1 409 516, Journal of Organic Chemistry 1970, 3£, 4217) wurdenIn 'various publications (French patent specification 1 409 516, Journal of Organic Chemistry 1970, £ 3, 4217) were
309833/ 1 1 39309833/1 1 39
•ungesättigte Halogensulfone, die durch Zugabe eines Arylsulfonylhalogenids zu eineia Diolefin in Gegenwart von Kupfer- oder Eisenverbindungen als Katalysator hergestellt wurden, beschrieben.• Unsaturated halosulfones, which by adding an arylsulfonyl halide to a single diolefin in the presence of copper or iron compounds as a catalyst.
Durch dieses Verfahren, angewandt auf Isopren^erhält man einzig und allein die Aryl-4—halogen-2-methyl-buten-2-yl-sulfone. Diese Sulfone sind isomere Produkte der erfindungsgemäßen Sulfone, die jedoch nicht das gleiche Interesse hinsichtlich der organischen Synthese besitzen und zwar aufgrund ihrer Struktur. Die erfindungsgemäßen Sulfone können bei der Synthese verschiedener terpenischer Verbindungen verwendet werden, wenn man an ein Molekül ein oder mehrere isoprenische Gruppierungen anbringen möchte.By this process, applied to isoprene, one obtains only and the aryl-4-halo-2-methyl-buten-2-yl sulfones alone. These sulfones are isomeric products of the sulfones according to the invention, which, however, are not of the same interest in terms of organic synthesis because of their structure. The sulfones of the invention can be used in the synthesis of various terpenic compounds can be used if you want to attach one or more isoprenic groups to a molecule.
Die Sulfone der Formel I, in denen X ein Halogenatom bedeutet, können auf einfache und praktische Weise hergestellt werden, indem man ein Alkalisulfinat der Formel E-SOoM, in der R die zuvor angegebene Bedeutung besitzt, und M ein Alkalimetall bedeutet, mit einem 1,4-Dihalogen-2-methyl-buten-2 umsetzt. Für diese letzteren Verbindungen wird man vorzugsweise das 1,4--Di chi or- oder das 1,4—Dibrom-2 -r.ethyl-buten-2 auswählen und für die SuIfinate wird man vorzugsweise Natrium oder Kaliumphenylsulfinat und die Chlorphenylsulfinate oder Tolylsulfonate dieser Alkalimetalle verwenden. The sulfones of the formula I in which X is a halogen atom, can be made in a simple and practical way by one an alkali metal sulfinate of the formula E-SOoM, in which R the previously Has given meaning, and M means an alkali metal, with a 1,4-dihalo-2-methyl-butene-2 reacted. For the latter Compounds are preferably the 1,4 - Di chi or the Select 1,4 — Dibromo-2-r. Ethyl-butene-2 and use for the SuIfinate one preferably uses sodium or potassium phenyl sulfinate and the chlorophenyl sulfinate or use tolylsulfonates of these alkali metals.
Zur Durchführung -der Reaktion genügt es, im wesentlichen äquimolekulare Mengen der beiden Reaktanten, vorzugsweise in einem Lösungsmittel wie Methanol, Äthanol oder A'thylenglykol zu mischen. Man hält die Reaktionsmasse bei mäßiger Temperatur, vorzugsweise zwischen O und 60°C. Die Umsetzung, die selektiv ist, gestattet es, das gewünschte Monosulfon mit guten Ausbeuten zu erhalten. To carry out the reaction, it is sufficient to have essentially equimolecular Mix amounts of the two reactants, preferably in a solvent such as methanol, ethanol or ethylene glycol. The reaction mass is kept at a moderate temperature, preferably between 0 and 60.degree. Implementation that is selective is allowed it is necessary to obtain the desired monosulfone in good yields.
Die Sulfone der Formel I, in der X eine Gruppe -SO2R bedeutet, können auspellend von Halogensulfonen der Formel I durch Umsetzung mit einem Alkalisulfinat der Formel RSO2M mit der vorstehend angegebenen Eedeutung hergestellt werden. Eine praktische MethodeThe sulfones of the formula I, in which X denotes a group -SO 2 R, can be prepared by pelleting halogen sulfones of the formula I by reaction with an alkali metal sulfinate of the formula RSO 2 M with the meaning given above. A practical method
309833/1139309833/1139
zur Durchführung·dieser Herstellung besteht darin, daß man unter Rückfluß im wesentlichen äquimolekulare Mengen des gewählten Sulfinats und des Halogensulfons (I) in einem Lösungsmittel wie Methanol oder Äthanol erwärmt.to carry out this preparation consists in that one essentially equimolecular amounts of the selected under reflux Sulfinate and the halogen sulfone (I) in a solvent heated like methanol or ethanol.
Diese Disulfone können für die Synthese verschiedener terpenischer Verbindungen verwendet werden. Setzt man sie mit einer terpenischen Verbindung ,. wie einem Halogenid, um und unterwirft darauf das Produkt einer Desulfonierungsbehandlung, so knüpft man an das Molekül des Ausgangsproduktes eine Isoprenkette an.These disulfones can be used for the synthesis of various terpenic Connections are used. Put them with a terpenic connection,. like a halide, around and subject then the product of a desulfonation treatment, so links an isoprene chain is attached to the molecule of the starting product.
Die folgenden Beispiele erläutern die Herstellung dieser Sulfone .The following examples illustrate the preparation of these sulfones .
Man-beläßt unter Rühren während 15 Stunden unter Stickstoff- · atmosphäre eine Mischung von 59 »1 S Natriumphenylsulfinat und 50 g 1,4-Dichlor-2-methyl-buten-2 in 294- cm wasserfreiem Äthanol, wobei die Temperatur auf 38°C geregelt ist. Man erhält eine heterogene weiße Masse, die man filtriert. Der auf dem Filter erhaltene Niederschlag wird mit Wasser gewaschen und anschließend aus absolutem Äthylalkohol umkristallisiert. Nach zwei aufeinander folgenden Umkristallisationen isoliert man 5^2 g eines weißen Feststoffes mit einem Schmelzpunkt von 1500C und 1,4- g einer Verbindung mit einem Schmelzpunkt von 88°C. Aus dem Filtrat, das in einem Kühlschrank aufbewahrt wurde, isoliert man durch zwei aufeinander folgende Umkristallisationen 4-5,3 έ? eines weißen Feststoffes mit einem Schmelzpunkt von 88°C. Dieser letztere rird durch Elementaranalyse, Infrarotspektrcs-A mixture of 59 »1 S sodium phenylsulfinate and 50 g of 1,4-dichloro-2-methyl-butene-2 in 294 cm of anhydrous ethanol is left with stirring for 15 hours under a nitrogen atmosphere, the temperature being 38 ° C is regulated. A heterogeneous white mass is obtained, which is filtered. The precipitate obtained on the filter is washed with water and then recrystallized from absolute ethyl alcohol. After two successive recrystallizations one 5 ^ 2 isolated g of a white solid having a melting point of 150 0 C and 1,4 g of a compound with a melting point of 88 ° C. From the filtrate, which has been kept in a refrigerator, 4-5.3 έ? of a white solid with a melting point of 88 ° C. This latter is determined by elemental analysis, infrared spectra
kopie und magnetische Kernresonanz als Phenyl-4— chlor-3-methylbuten-2-yl-sulfon identifiziert. Die Ausbeute beträgt 60 % in bezug auf das eingesetzte Dichlorderivat.and nuclear magnetic resonance identified as phenyl-4- chloro-3-methylbuten-2-yl-sulfone. The yield is 60 % based on the dichloro derivative used.
Das-Produkt vom Schmelzpunkt 1500C ist das 1,4~bis(Phenylsul-The product with a melting point of 150 ° C. is the 1,4 bis (phenyl sulf
3098 3 3/11393098 3 3/1139
Mt _ Mt _
f onyl )-2-methyl*-buten-2.f onyl) -2-methyl * -butene-2.
■χ
Man erhitzt unter Rückfluß auf 80° in einem 250 cnr Kolben, der
mit einer Rührvorrichtung und einem Kühler versehen ist, während 4- Stunden ein Gemisch von 6 g Phenyl-4— chlor-3-methyl-buben-2-ylsulfon
(0,025 Mol), 4,9 g Natriumphenylsulfinat (0,029 Mol)
50 cur absolutem Äthylalkohol. Man kühlt darauf auf 200C ab,,
filtriert anschließend den gebildeten Niederschlag und wäscht zweimal mit 5 cm Äthylalkohol. Der niederschlag, wird auf dem
Filter mit I50 cm destilliertem Wasser gewaschen und man erhält
nach Trocknen 6,5 g eines weißen Produktes mit einem
Schmelzpunkt von 1500C, das durch Infrarotspektroskopie und
magnetische Kernresonanz als das 1,A—bis(Phenylsulfonyl)-2-methyl-buten-2
identifiziert wird. Die vereinigten alkoholischen Lösungen ergeben durch Abkühlen nochmals 0,2 g desselben Produktes.
Ausbeute 78 %. ■ χ
A mixture of 6 g of phenyl-4- chloro-3-methyl-buben-2-ylsulfone (0.025 mol ), 4.9 g sodium phenylsulfinate (0.029 mol)
50 cur of absolute ethyl alcohol. It is then cooled to 20 0 C,
then filtered the precipitate formed and washed twice with 5 cm ethyl alcohol. The precipitate is washed on the filter with 150 cm of distilled water and, after drying, 6.5 g of a white product with a
Melting point of 150 0 C, which by infrared spectroscopy and
nuclear magnetic resonance is identified as the 1, A-bis (phenylsulfonyl) -2-methyl-butene-2. The combined alcoholic solutions give another 0.2 g of the same product on cooling. Yield 78 %.
309833/1138309833/1138
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7203481A FR2171496A5 (en) | 1972-02-02 | 1972-02-02 | 4-chloro-and 4-organosulphonyl-3-methyl-2-buten - -1-yl sulphones - useful source of isoprene units for syntheses |
| FR7209398A FR2179271A6 (en) | 1972-03-17 | 1972-03-17 | 4-chloro-and 4-organosulphonyl-3-methyl-2-buten - -1-yl sulphones - useful source of isoprene units for syntheses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2305235A1 true DE2305235A1 (en) | 1973-08-16 |
Family
ID=26216881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732305235 Pending DE2305235A1 (en) | 1972-02-02 | 1973-02-02 | NEW ISOPRENIC SULPHONES |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4885532A (en) |
| BE (1) | BE794871A (en) |
| CH (1) | CH557334A (en) |
| DD (1) | DD108077A5 (en) |
| DE (1) | DE2305235A1 (en) |
| GB (1) | GB1396626A (en) |
| IT (1) | IT972673B (en) |
| NL (1) | NL7301102A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030076243A (en) * | 2001-02-06 | 2003-09-26 | 스미또모 가가꾸 고오교오 가부시끼가이샤 | Novel sulfone derivatives and process for producing these |
| EP1231197A1 (en) * | 2001-02-07 | 2002-08-14 | Sumitomo Chemical Company, Limited | Process for producing allyl halide compound |
| CN1264815C (en) * | 2001-10-31 | 2006-07-19 | Sk株式会社 | Method of preparing 4-chloro-3-methyl-2-butenylphenyl sulfide, di4-chloro-3-methyl-2-butenylsulfide and di4-chloro-3-methyl-2-butenylsulfone for synthesis of natural carotenoid products |
| DE102009056731A1 (en) | 2009-12-04 | 2011-06-09 | Rev Renewable Energy Ventures, Inc. | Halogenated polysilanes and polygermanes |
-
0
- BE BE794871D patent/BE794871A/en unknown
-
1972
- 1972-12-20 IT IT3329872A patent/IT972673B/en active
-
1973
- 1973-01-25 NL NL7301102A patent/NL7301102A/xx active Search and Examination
- 1973-01-30 DD DD16853073A patent/DD108077A5/xx unknown
- 1973-01-31 JP JP1211873A patent/JPS4885532A/ja active Pending
- 1973-02-01 CH CH143373A patent/CH557334A/en not_active IP Right Cessation
- 1973-02-02 DE DE19732305235 patent/DE2305235A1/en active Pending
- 1973-02-02 GB GB537173A patent/GB1396626A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE794871A (en) | 1973-08-01 |
| IT972673B (en) | 1974-05-31 |
| NL7301102A (en) | 1973-08-06 |
| JPS4885532A (en) | 1973-11-13 |
| DD108077A5 (en) | 1974-09-05 |
| CH557334A (en) | 1974-12-31 |
| GB1396626A (en) | 1975-06-04 |
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