synthesis of aspirin - umsl：umsl合成阿司匹林

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1、PharmacologicallyactivecompoundsOverhistory,manycompoundsobtainedfromnaturehavebeenusedtocureillsortoproduceaneffectinhumans.Thesenaturalproductshavebeenobtainedfromplants,minerals,andanimals.Inaddition,varioustransformationsoftheseandothercompoundsh

2、aveledtoevenmoremedicallyusefulcompounds.Duringthissemester,youwillhaveanopportunitytoisolatesomepharmacologicallyactivenaturalproductsandtosynthesizeotheractivecompoundsfromsuitablestartingmaterials.Analgesicsarecompoundsusedtoreducepain,antipyretic

3、sarecompoundsusedtoreducefever.Onepopulardrugthatdoesbothisaspirin.TheMerckIndex,whichisanenclopediaofchemicals,drugsandbiologicals,liststhefollowinginformationunderaspirin:acetylsalicylicacid;monoclinictabletsorneedle-likecrystals;mp135(rapidheating

4、);isodorless,butinmoistairitisgraduallyhydrolyzedintosalicylicandaceticacids;onegramdissolvesin300mLofwaterat25o,in100mLofwaterat37o,in5mLalcohol,in17mLchloroform.SYNTHESISOFASPIRIN(acetylsalicylicacid)1.Place2.Og(O.O15mole)ofsalicylicacidina125mLEr

5、lenmeyerflask.2.Add5mL(O.O5mole)ofaceticanhydride,followedby5dropsofconc.H2SO4(useadropper,H2SO4ishighlycorrosive)andswirltheflaskgentlyuntilthesalicylicaciddissolves.3.Heattheflaskgentlyonthesteambathforatleast10minutes.4.Allowtheflasktocooltoroomte

6、mperature.Ifacetylsalicylicaciddoesnotbegintocrystallizeout,scratchthewallsoftheflaskwithaglassrod.Coolthemixtureslightlyinanicebathuntilcrystallizationiscompleted.Theproductwillappearasasolidmasswhencrystallizationiscompleted.5.Add50mLofwaterandcool

7、themixtureinanicebath.Donotaddthewateruntilcrystalformationiscomplete.6.VacuumfiltertheproductusingaBuchnerfunnel.YoucanusesomeofthefiltratetorinsetheErlenmeyerflaskifnecessary.7.Rinsethecrystalsseveraltimeswithsmallportions(5mL)ofcoldwaterandairdryt

8、hecrystalsonaBuchnerfunnelbysuctionuntilthecrystalsappeartobefreeofsolvent.Testthiscrudeproductforthepresenceofunreactedsalicylicacidusingtheferricchloridetest.Recordtheweightofthecrudesolidwhichprobablycontainswater.188.Stirthecrudesolidwith25mLofas