DE856148C - Process for the preparation of 1-oxy-5, 6, 7, 8-tetrahydronaphthalenes halogenated in the 4-position - Google Patents

Process for the preparation of 1-oxy-5, 6, 7, 8-tetrahydronaphthalenes halogenated in the 4-position

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Publication number
DE856148C
DE856148C DED4256D DED0004256D DE856148C DE 856148 C DE856148 C DE 856148C DE D4256 D DED4256 D DE D4256D DE D0004256 D DED0004256 D DE D0004256D DE 856148 C DE856148 C DE 856148C
Authority
DE
Germany
Prior art keywords
oxy
tetrahydronaphthalenes
tetrahydronaphthalene
halogenated
preparation
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
Application number
DED4256D
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German (de)
Inventor
Winfried Dr Hentrich
Jakob Dr Wilh Kaiser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Deutsche Hydrierwerke AG
Original Assignee
Deutsche Hydrierwerke AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Deutsche Hydrierwerke AG filed Critical Deutsche Hydrierwerke AG
Priority to DED4256D priority Critical patent/DE856148C/en
Application granted granted Critical
Publication of DE856148C publication Critical patent/DE856148C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von in 4-Stellung halogenierten 1-Oxy-5, 6, 7, 8-tetrahydronaphthalinen Es wurde gefunden, daß man ausgezeichnete Desinfektionsmittel erhält, die den üblichen P'he- nolen hinsichtlich Wirksamkeit weit überlegen sind, wenn man i-Oxv-3. 6, 7, e-tetrahydronaphthalin oder desSeti 2-:\11,\-l- 1>7w. 2-Halogetisubstitutions- produkte in an sich bekannter Weise mit balogienie- renden Mitteln behandelt, wobei i Halogenatom in die .-Stellung des :\usgattgsstoffes eintritt. Für die Halogenierung kommen in erster Linie in Be- tracht: t-Oxv-@. 6, 7, 8-tetrahydronaphtlialin, i-Oxy-2-metlivl-5, b, 7, 8-tetrahydronaphtlialin und i-Oxv-2-chlor-5, 6, 7, 8-tetrahydronaphthalin sowie diejenigen Substitutionsprodukte dieser Verbin- dtttigen. welche iti 4-Stellung durch Halogen ersetz- bare Substituenten, wie Sulfo-, Carboxyl-, Nitro-oder Acylaminogruppen enthalten. Als halogenierende Mittel sind alle diejenigen geeignet, die üblicherweise zur Halogen.ierung von Phenolen zur :\nwendung kommen. Beispielsweise seien genannt: Chlor, Brom in flüssiger oder Dampfform oder Jod, Mischungen von Permanganat und Halogenwasserstoff säure, Sulfurylchlori-d. Pliosphoroxychlorid und dergleichen. In das unsubstituierte i-Oxy-,s, 6, 7, 8-tetrahydronaphthalin kann man je nach der angewandten Menge an Halogenierun.gsmitteln i oder mehrere Halogenatome einführen. Bei Verwendung von Sulfurvlchlorid gelingt es, vornehmlich die Halogenierung in p-Stellung zur Hydroxylgruppe "durchzuführen, so daß das 4-Chlor-i-oxy-5, 6, 7, 8-tetrahydronaphthalin entsteht, welches sich durch weitere Halogenierung in die 4-C'hlor-2=halogen-i-oxy-5, 6, 7, 8-tetrahydronaphthaline überführen läßt.Process for the preparation of 1-oxy-5, 6, 7 , 8-tetrahydronaphthalenes halogenated in the 4-position It has been found to be excellent Receives disinfectants that have the usual P'he- noles are far superior in terms of effectiveness, when using i-Oxv-3. 6, 7, e-tetrahydronaphthalene or desSeti 2 -: \ 11, \ - l- 1> 7w. 2-halogen substitution products in a manner known per se with balogienie- generating agents, where i is halogen atom enters the.-position of: \ usgattgsstoffes. For halogenation come primarily into costume: t-Oxv- @. 6, 7, 8-tetrahydronaphtlialin, i-Oxy-2-metlivl-5, b, 7, 8-tetrahydronaphtlialin and i-Oxv-2-chloro-5, 6, 7, 8-tetrahydronaphthalene and those substitution products of these compounds dttttter. which iti 4-position to be replaced by halogen contain bare substituents such as sulfo, carboxyl, nitro or acylamino groups. Suitable halogenating agents are all those that are commonly used for halogenating phenols. Examples include: chlorine, bromine in liquid or vapor form or iodine, mixtures of permanganate and hydrohalic acid, sulfurylchloride. Phosphorus oxychloride and the like. Depending on the amount of halogenating agents used, one or more halogen atoms can be introduced into the unsubstituted i-oxy-, 6, 7, 8-tetrahydronaphthalene. When using sulfur chloride it is possible to carry out mainly the halogenation in the p-position to the hydroxyl group, so that the 4-chloro-i-oxy-5, 6, 7, 8-tetrahydronaphthalene is formed, which is converted into the 4- C'hlor-2 = halogen-i-oxy-5, 6, 7, 8-tetrahydronaphthalenes can be converted.

'Beispiel 66o Gewichtsteile i-Oxy-5, 6, 7, 8-tetrahydronaphthalin (F. = 65 bis 67°) werden in 16oo Gewichtsteilen Tetrachlorkohlenstoff gelöst und innerhalb von 3 Stunden mit 66o Gewichtsteilen Sulfurylchlorid bei 30 bis 40° versetzt. Sodann wird die Temperatur allmählich gesteigert und die Reaktionsmasse schließlich 2 Stunden am Rückflußkühler zum Sie-den erhitzt. Durch Destillation werden die Hilfsstoffe nunmehr abgetrennt und das Reaktionsprodukt unter 23 mm Hg-Druck bei 175 bis 178° überdestilliert. Es erstarrt beim Abkühlen zu einer farblosen Kristallmasse, die nach dem Umkristallisieren aus Benzin bei 78 bis 79' schmilzt. Die Ausbeute an i-Oxy-4-chlor-5, 6, 7, 8-tetrahydronaphthalin beträgt etwa 75 °/o der Theorie. Geringe Mengen an 1-Oxy-2-chlor-5, 6, 7, 8-tetrahydronaphthalin können aus der Mutterlauge des Benzins gewonnen werden und durch Nachchlorierung in das i-Oxy-2, 4-dichlor-5, 6, 7, 8-tetrahydronaphthalin übergeführt werden, das man auch erhält, wenn man größere Mengen Sulfurylchlorid auf die i-Oxyverbindung einwirken läßt. Die Behandlung der 2-Chlor-i-oxyver-bindung mit Brom führt zum 1-Oxy-2-chlor-4-brOm-5, 6, 7, 8-tetrahydronaphthalin.Example 66o parts by weight of i-oxy-5, 6, 7, 8-tetrahydronaphthalene (m.p. 65 to 67 °) are dissolved in 1600 parts by weight of carbon tetrachloride and 66o parts by weight of sulfuryl chloride at 30 to 40 ° are added over the course of 3 hours. The temperature is then gradually increased and the reaction mass is finally heated to boiling point in the reflux condenser for 2 hours. The auxiliaries are now separated off by distillation and the reaction product is distilled over under 23 mm Hg pressure at 175 to 178 °. On cooling it solidifies to a colorless crystal mass which, after recrystallization from gasoline, melts at 78 to 79 '. The yield of i-oxy-4-chloro-5, 6, 7, 8-tetrahydronaphthalene is about 75% of theory. Small amounts of 1-oxy-2-chloro-5, 6, 7, 8-tetrahydronaphthalene can be obtained from the mother liquor of gasoline and converted into i-oxy-2, 4-dichloro-5, 6, 7, 8 by post-chlorination -tetrahydronaphthalene can be converted, which is also obtained if larger amounts of sulfuryl chloride are allowed to act on the i-oxy compound. Treatment of the 2-chloro-i-oxyver compound with bromine leads to 1-oxy-2-chloro-4-brOm-5, 6, 7, 8-tetrahydronaphthalene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von in 4-Stellung halogenierten i - Oxy - 5, 6, 7, 8 - tetrahydronaphthalinen, dadurch gekennzeichnet, daß man das i-Oxy-5, 6, 7, 8-tetrahydronaphthalin, das in 2-Stellung sowie in 4-Stellung durch Halogen ersetzbare Substituenten enthalten kann, in an sich bekannter Weise mit halogenierenden Mitteln behandelt.PATENT CLAIM: Process for the production of halogenated in the 4-position i - Oxy - 5, 6, 7, 8 - tetrahydronaphthalenes, characterized in that the i-Oxy-5, 6, 7, 8-tetrahydronaphthalene, which in the 2-position and in the 4-position by Halogen can contain replaceable substituents, in a manner known per se treated with halogenating agents.
DED4256D 1939-10-15 1939-10-15 Process for the preparation of 1-oxy-5, 6, 7, 8-tetrahydronaphthalenes halogenated in the 4-position Expired DE856148C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED4256D DE856148C (en) 1939-10-15 1939-10-15 Process for the preparation of 1-oxy-5, 6, 7, 8-tetrahydronaphthalenes halogenated in the 4-position

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED4256D DE856148C (en) 1939-10-15 1939-10-15 Process for the preparation of 1-oxy-5, 6, 7, 8-tetrahydronaphthalenes halogenated in the 4-position

Publications (1)

Publication Number Publication Date
DE856148C true DE856148C (en) 1952-11-20

Family

ID=7030914

Family Applications (1)

Application Number Title Priority Date Filing Date
DED4256D Expired DE856148C (en) 1939-10-15 1939-10-15 Process for the preparation of 1-oxy-5, 6, 7, 8-tetrahydronaphthalenes halogenated in the 4-position

Country Status (1)

Country Link
DE (1) DE856148C (en)

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