DE362751C - Process for the preparation of coumarins - Google Patents

Process for the preparation of coumarins

Info

Publication number
DE362751C
DE362751C DEP41474D DEP0041474D DE362751C DE 362751 C DE362751 C DE 362751C DE P41474 D DEP41474 D DE P41474D DE P0041474 D DEP0041474 D DE P0041474D DE 362751 C DE362751 C DE 362751C
Authority
DE
Germany
Prior art keywords
coumarins
preparation
acid
phenols
finished
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
DEP41474D
Other languages
German (de)
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.)
WOLFGANG PONNDORF DR
Original Assignee
WOLFGANG PONNDORF DR
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
Priority to DE1919338737D priority Critical patent/DE338737C/en
Application filed by WOLFGANG PONNDORF DR filed Critical WOLFGANG PONNDORF DR
Priority to DEP41474D priority patent/DE362751C/en
Priority to DEP42186D priority patent/DE362752C/en
Application granted granted Critical
Publication of DE362751C publication Critical patent/DE362751C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)

Description

Verfahren zur Darstellung von Cumarinen. Nach dem in dem Patent 338737 beschriebenen Verfahren zur Darstellung von Cumarinen werdell Phenole mit Furnarsäure oder Maleinsäure bei Gegenwart von Schwefelsäure kondensiert. Es hat sich nun herausgestellt, daß an Stelle eines Gemisches von Schwefelsäure und Phenol mit bestem Erfolge solche fertigen Sulfosäuren von Pheno,len verwendet werden können, die, wie z. B. die p-Kresc>Idisulfosäure die Sulfogruppen leicht verlieren.Process for the preparation of coumarins. According to the process described in patent 338737 for the preparation of coumarins, phenols are condensed with furnaric acid or maleic acid in the presence of sulfuric acid. It has now been found that, instead of a mixture of sulfuric acid and phenol, such finished sulfonic acids of phenol can be used with the best results, such as. B. the p-cresc> idisulfonic acid easily lose the sulfo groups.

Ein Zusatz eines Kondensationsmittels ist dann nicht notwendig, da die Sulfosäure gleichzeitig als Katalysator wirkt.An addition of a condensing agent is then not necessary because the sulfonic acid also acts as a catalyst.

B.ei spi el.Example.

27oTeile p-Kresoldisulfosäure und iooTeile Maleinsäure werden im Rührwerk 75 Minuten auf 16o' erhitzt. Nach Eingießen der Reaktionsmasse in Wasser wird das gebildete 6-Methylcumarin mit Wasserdampf abgetrieben.27o parts of p-cresol disulphonic acid and 100 parts of maleic acid are heated to 16o for 75 minutes in a stirrer. After the reaction mass has been poured into water, the 6-methylcoumarin formed is driven off with steam.

Claims (1)

PATENT-ANSPRUCH: Abänderung des durch Patent 338737 geschützten Verfahrens zur Darstellung von Cumarinen, dadurch gekennzeichnet, daß an Stelle der Gemische von Phenolen und Schwefelsäure fertige, die Sulfogruppen leicht verlierende, Phenolsulfo--säuren mit Fumarsäure oder Maleinsäure oder deren Derivaten auf Temperaturen über i:2o' erhitzt werden.PATENT CLAIM: Modification of the process for the preparation of coumarins protected by patent 338737 , characterized in that, instead of the mixtures of phenols and sulfuric acid, finished phenolsulfonic acids with fumaric acid or maleic acid or their derivatives are reduced to temperatures above i : 2o 'to be heated.
DEP41474D 1921-02-17 1921-02-17 Process for the preparation of coumarins Expired DE362751C (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE1919338737D DE338737C (en) 1921-02-17 1919-11-18 Process for the preparation of coumarins
DEP41474D DE362751C (en) 1921-02-17 1921-02-17 Process for the preparation of coumarins
DEP42186D DE362752C (en) 1921-02-17 1921-02-17 Process for the production of coumarins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP41474D DE362751C (en) 1921-02-17 1921-02-17 Process for the preparation of coumarins

Publications (1)

Publication Number Publication Date
DE362751C true DE362751C (en) 1922-10-31

Family

ID=7377864

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP41474D Expired DE362751C (en) 1921-02-17 1921-02-17 Process for the preparation of coumarins

Country Status (1)

Country Link
DE (1) DE362751C (en)

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