DE714848C - Process for the preparation of an oxotetrahydronaphthalene - Google Patents

Process for the preparation of an oxotetrahydronaphthalene

Info

Publication number
DE714848C
DE714848C DEI64443D DEI0064443D DE714848C DE 714848 C DE714848 C DE 714848C DE I64443 D DEI64443 D DE I64443D DE I0064443 D DEI0064443 D DE I0064443D DE 714848 C DE714848 C DE 714848C
Authority
DE
Germany
Prior art keywords
oxotetrahydronaphthalene
preparation
acid
methoxynaphthalene
dihydro
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
DEI64443D
Other languages
German (de)
Inventor
Dr Walter Salzer
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI64443D priority Critical patent/DE714848C/en
Application granted granted Critical
Publication of DE714848C publication Critical patent/DE714848C/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties

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

Description

Verfahren zur Herstellung eines Oxotetrahydronaphthalins Nach dem Verfahren des Patents 708 114 erhält man durch Einwirken von Benzopersäure auf 3, 4-Dihydro-6-methoxynaphthalin neben dem 1, 2, 3, 4-Tetrahydro-r. 2-oxydo-6-m-ethoxynaphthalin beträchtliche Mengen vou 2-Keto-r, z, 3, 4-tetrahydro-6=methoxynaphthalin.Process for the production of an oxotetrahydronaphthalene According to the process of the patent 708 114, by the action of benzoperic acid on 3,4-dihydro-6-methoxynaphthalene in addition to the 1,2,3,4-tetrahydro-r. 2-oxydo-6-m-ethoxynaphthalene considerable amounts of 2-keto-r, z, 3, 4-tetrahydro-6 = methoxynaphthalene.

Gemäß vorliegender Erfindung kann man bei der genannten Umsetzung an Stelle von Benzopersäure .auch Phthalopersäure als Oxydationsmittel verwenden. Die Abtrennung des gebildeten Ketons erfolgt auch im vorliegenden Falle zweckmäßig mittels der Bisulfitverbindung.According to the present invention, one can in the aforementioned reaction Instead of benzoperic acid, also use phthaloperic acid as an oxidizing agent. The ketone formed is also expediently separated off in the present case by means of the bisulfite compound.

Beispiel In Zoo ccm einer 1o,9 g Phthalopersäure enthaltenden .ätherischen Lösung werden bei o bis 5' 8 g 3. 4-Dihydro-6-methox},naphthalin eingetragen. Nach 12stündigem Stehen in Eiswasser wird die ätherische Lösung mit 2 n-Natronlauge und anschließend mit,Wasser gewaschen. Dann wird die ätherische Lösung mit einer konzentrierten wäßrigen Bisulfitläsung geschüttelt. Dabei scheidet sich die Bisulfitverbindung des 2-Keto-r, 2, 3, 4-tetra hydro-6-methoxynaphthalins kristallin ab. Die weitere Aufarbeitung erfolgt nach der Arbeitsweise des Patents 70811:1. Die Ausbeute am. 2-Keto-1, 2, 3, 4-tetrahydro-6=methoxynaphthalin beträgt etwa 3 o ojo .EXAMPLE 8 g of 3,4-dihydro-6-methoxy-naphthalene are introduced into zoo ccm of an ethereal solution containing 10.9 g of phthaloperic acid at 0 to 5 '. After standing in ice water for 12 hours, the ethereal solution is washed with 2N sodium hydroxide solution and then with water. Then the ethereal solution is shaken with a concentrated aqueous bisulfite solution. The bisulfite compound of 2-keto-r, 2, 3, 4-tetra hydro-6-methoxynaphthalene separates out in crystalline form. The further processing takes place according to the procedure of patent 70811: 1. The yield of 2-keto-1, 2, 3, 4-tetrahydro-6 = methoxynaphthalene is about 30%.

Claims (1)

PATENTANSPRUCH: Weitere Ausbildung des Verfahrens zur Herstellung :eines Oxotetrahydronaphthalins, .dadurch gekennzeichnet, daß man bei der nach dem Patent 708 11:1 bewirkten Oxydation von 3, 4-Dihydro.-6=metlioxynaphthalin an Stelle von Benzopersäure als Oxydationsmittel Phthalopersäure verwendet.PATENT CLAIM: Further development of the process for producing: a Oxotetrahydronaphthalins, .dadurch in that in accordance with the Patent 708 11: used effected 1 oxidation of 3, 4-Dihydro.-6 = metlioxynaphthalin instead of perbenzoic acid as the oxidizing agent Phthalopersäure.
DEI64443D 1939-04-28 1939-04-28 Process for the preparation of an oxotetrahydronaphthalene Expired DE714848C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI64443D DE714848C (en) 1939-04-28 1939-04-28 Process for the preparation of an oxotetrahydronaphthalene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI64443D DE714848C (en) 1939-04-28 1939-04-28 Process for the preparation of an oxotetrahydronaphthalene

Publications (1)

Publication Number Publication Date
DE714848C true DE714848C (en) 1941-12-08

Family

ID=7196123

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI64443D Expired DE714848C (en) 1939-04-28 1939-04-28 Process for the preparation of an oxotetrahydronaphthalene

Country Status (1)

Country Link
DE (1) DE714848C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE956508C (en) * 1953-10-02 1957-01-17 Takeda Pharmaceutical Process for the preparation of dihydrosantonine pellets

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE956508C (en) * 1953-10-02 1957-01-17 Takeda Pharmaceutical Process for the preparation of dihydrosantonine pellets

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