CH89340A - Process for the preparation of trimethylacetylsalicylic acid. - Google Patents

Process for the preparation of trimethylacetylsalicylic acid.

Info

Publication number
CH89340A
CH89340A CH89340DA CH89340A CH 89340 A CH89340 A CH 89340A CH 89340D A CH89340D A CH 89340DA CH 89340 A CH89340 A CH 89340A
Authority
CH
Switzerland
Prior art keywords
sep
acid
preparation
trimethylacetylsalicylic
triniethyl
Prior art date
Application number
Other languages
German (de)
Inventor
Farbenfabriken Vorm Friedr Co
Original Assignee
Farbenfab Vorm Bayer F & Co
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 Farbenfab Vorm Bayer F & Co filed Critical Farbenfab Vorm Bayer F & Co
Publication of CH89340A publication Critical patent/CH89340A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Description

  

  Verfahren zur Darstellung     von        Trimethylacetylsalieylsäure.       Es wurde gefunden, dass man die noch  nicht bekannte     Trimethy        lacetylsalicyls;iure    da  durch erhalten kann, dass man die     Trimethyl-          essigsäure    mit     Salicylsäure    verestert.  



  Die     Triniethylacety        lsalicylsäur-e    ist ein gut  kristallisierender, fester Körper. Sie zeigt  neben den bekannten antirheumatischen und       analgetischen        Eigenschaften    der     AcetyIsalic5#1-          säure    stark ausgesprochene     diuretiselie        Wir-          kungen.    Sie ist fast geschmacklos     und    wird  gut vertragen.

      <I>Beispiel:</I>    Zu einer     Liisung    von 138     Gewichtsteilen          Salicylsäure,    200     Gewichtsteilen        trockenem     Äther und 83     Glewichtsteilen        Pyridin    wer  den unter Rühren und Kühlen langsam 126 Ge  wichtsteile     Triniethylossigsäurecliloi-i < 1    gegeben  und das     sseaktionsgeniiseh    unter zeitweiligem  Durchrühren zwei Tage bei     gewöhnlicher    Tem  peratur stehen gelassen, wobei     das    zunächst  ölig ausgefallene Produkt erstarrt.

   Darauf  wird der Äther     miiglicbst        vollstündig    verjagt.    der Rückstand mit Wasser     durchgerührt    und  das zu einem weilen Kristallbrei erstarrende       Gemisch    zur Entfernung     von    etwa noch vor  handenem     Pyridin    und salzsaurem     Pyridin     abgesaugt und an der Luft     getrocknet.    Die  Ausbeute an     roher    lufttrockener     Trymethyl-          acetylsalieyis:iure        betragt        95-98         ;-@    der Theo  rie.

   Zur     Ileinigung    wird<I>die</I> rohe Säure aus  wenig Eisessig bei     Wasserhadteiuperatur    um  kristallisiert. Der beim Erkalten     erhaltene,     dicke Brei     feiner,        weisser.    nadelförmiger Blätt  chen wird darauf abgesaugt, mit etwas Benzol  nachgewaschen und bei etwa     90"    getrocknet.  Die reine     Trirnethylacetylsalicylsüure    schmilzt  bei     1'.35 .    Sie gibt mit     Eiseneliloridliisung     keine     lZeaktion.  



  Process for the preparation of trimethylacetylsalicic acid. It has been found that the as yet unknown trimethyl acetylsalicylic acid can be obtained by esterifying the trimethyl acetic acid with salicylic acid.



  Triniethylacety lsalicylsäur-e is a solid body that crystallizes well. In addition to the well-known anti-rheumatic and analgesic properties of AcetyIsalic5 # 1 acid, it shows pronounced diuretic effects. It is almost tasteless and well tolerated.

      <I> Example: </I> To a solution of 138 parts by weight of salicylic acid, 200 parts by weight of dry ether and 83 parts by weight of pyridine, 126 parts by weight of tri-diethylosetic acid are slowly added while stirring and cooling, and the reaction mixture is added for two days with occasional stirring The usual tem perature left to stand, the initially oily product solidified.

   The ether is then chased away completely. the residue was stirred through with water and the mixture, which solidified to form an occasional crystal slurry, was filtered off with suction to remove any pyridine and hydrochloric acid pyridine and dried in the air. The yield of crude, air-dry trymethyl acetyl salicylic acid is 95-98; - @ of the theory.

   For purification, <I> the </I> crude acid is recrystallized from a little glacial acetic acid at water temperature. The thick pulp obtained on cooling is finer, whiter. The needle-shaped leaflets are then sucked off, washed with a little benzene and dried at about 90 ". The pure trimethyl acetylsalicylic acid melts at 1.35. It does not react with iron chloride solution.

Claims (1)

EMI0001.0053 PATENTANSPRUCH: <tb> Verfahren <SEP> zur <SEP> Darstellung <SEP> der <SEP> Triniethyl acctyl@alicyl@äure, <SEP> darin <SEP> bestehend, <SEP> dass <SEP> inan <tb> Triniethylessigsäure <SEP> initSalicy <SEP> lsürireverestert. <tb> Die <SEP> 1.'rimethvlacet;vlsaliev <SEP> lsü@ue <SEP> ist <SEP> ein <SEP> gut <tb> kristallisierender. <SEP> fester <SEP> hiirlier. <SEP> der <SEP> bei <SEP> 135 schmilzt und mit Eisenchlorid keine Reaktion gibt. EMI0001.0053 PATENT CLAIM: <tb> Method <SEP> for <SEP> representation <SEP> of the <SEP> triniethyl acctyl @ alicyl @ acid, <SEP> in it <SEP>, <SEP> that <SEP> inan <tb> triniethyl acetic acid <SEP> initSalicy <SEP> isurire-esterified. <tb> The <SEP> 1.'rimethvlacet; vlsaliev <SEP> lsü @ ue <SEP> is <SEP> a <SEP> good <tb> more crystallizing. <SEP> firm <SEP> here. <SEP> the <SEP> at <SEP> 135 melts and does not react with ferric chloride. Sie zeigt rieben den bekannten anti rheumatischen und analgetischen Eigenschaf ten der Acetylsalicylsäure stark ausgespro- chene diuretische Wirlzungen. Sie ist fast geschmacklos und wird gut vertragen. It shows the well-known anti-rheumatic and analgesic properties of acetylsalicylic acid with strongly pronounced diuretic effects. It is almost tasteless and well tolerated.
CH89340D 1918-02-05 1919-02-03 Process for the preparation of trimethylacetylsalicylic acid. CH89340A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE337733T 1918-02-05

Publications (1)

Publication Number Publication Date
CH89340A true CH89340A (en) 1921-05-16

Family

ID=6221791

Family Applications (1)

Application Number Title Priority Date Filing Date
CH89340D CH89340A (en) 1918-02-05 1919-02-03 Process for the preparation of trimethylacetylsalicylic acid.

Country Status (2)

Country Link
CH (1) CH89340A (en)
DE (1) DE337733C (en)

Also Published As

Publication number Publication date
DE337733C (en) 1921-06-04

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