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Synthesis of acetylsalicylic acid (Aspirin) via the acidic acetylation of salicylic acidMeltrick R. Torres, Anthea Jae O. Ungsod, Jacquelyn Faye S. Usero,

Bryan Paul B. Uy, Roi Marion H. Uy, Grou no. !, "G# Faculty o$ %har&acyOrganic 'he&istry (a)oratory, Uni*ersity o$ Santo To&as

ABSTRACTOrganic synthesis is the rocess +here a desired organic co&ound is constructed or reared $ro& co&&erciallya*aila)le &aterials. The o)ecti*e o$ organic synthesis is to design the si&lest synthetic routes to a &olecule.

Acetylsalicylic acid, also kno+n as asirin, is one o$ the &ost +idely used &edications to reduce $e*er and is also usedas a ainkiller. -t is an acetyl deri*ati*e o$ salicylic acid. -t is a +hite, crystalline, +eakly acidic su)stance +hich &eltsat /01'. 2our t+o ri&ary o)ecti*es in this e3eri&ent +ill )e to synthesi4e and analy4e asirin.

INTR!UCTIN

Asirin is synthesi4ed through the reaction o$salicylic acid +ith acetyl anhydride, +hich causesa che&ical reaction that turns salicylic acid5shydro3yl grou into an acetyl grou, 6R7OH R7O'O'H/8. For the reaction to take lace, aninorganic acid such as hoshoric acid is used asa catalyst.

Asirin is &ost +idely sold o*er#the#counterdrug. -t has the a)ility to reduce $e*er 6anantiyretic8, to reduce ain 6an analgesic8, and toreduce s+elling, soreness, and redness 6an anti#in$la&&atory agent8. One o$ the $irst recorded

accounts $or the disco*ery o$ asirin aeared in9ngland, in :;/, crediting the )ark o$ +illo+trees +ith a )ene$icial e$$ect in alle*iating distressdue to $e*ers, aches, and ains. (ater, theco&ound salicylic acid 6na&ed $or the (atin+ord $or +illo+, sali38 +as isolated $ro& +illo+)ark. -t ro*ed to )e the acti*e ingredient. and di$$erentiate acetylsalicylic acid$ro& salicylic acid )y si&le che&ical tests.These test are? Reaction o$ Acetic Anhydride andSalicylic Acid, Starch Test, and Ferric 'hlorideTest.

"#P"RI$"NTA%

A. Co&pound test or sa&ples usedThe reagents or sa&le used +ere salicylicacid, acetic anhydride, @MnO, Fe'l/, and-odine solution.

B. Procedure

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The dried ASA +eight +as &easured andercentage yield +as co&uted.

. erric chloride Test for Salicylic Acid

; test tu)es +ere reared containing &l eacho$ distilled +ater. 'orresonding sa&les +erelaced on the ; test tu)es. On test tu)e ? acrystal o$ salicylic acid +as the sa&le, on test

tu)e "? a o+dered co&&ercial acetyl salicylicacid +as the sa&le, on test tu)e /? thesynthesi4e acetyl salicylic acid +as the sa&le, ontest tu)e ? )en4oic acid +as the sa&le, on testtu)e 0? a &l o$

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Ta-le '.+ Recovery !ata of recrystallied

aspirin

BS"R/ATINSBeight o$ +atch glass Dsalicylic acid E!.! g

Beight o$ e&ty +atchglass E;.!g

Beight o$ salicylic acid ".=g

olu&e o$ aceticanhydride 0.= &l

olu&e o$ concentratedsul$uric acid 0&l

Beight o$ $ilter aer Droduct /.:g

Beight o$ dry $ilter aer .:g

Beight o$ roduct ".= g

Theoretical 2ield ".;g

Actual 2ield ".=g

C 2ield :;.;C

Ta-le '.0. $eltin, point deter&ination

SAM%(9 M9(T-G %O-T RAG961'8

'rude asirin =;#"

Recrystalli4ed asirin #!

Ta-le '.1 !ifferentiation of startin, &aterialfro& the product

T"ST S2NT3"SI4"

! ASPIRIN

SA%IC2%IC

ACI!@MnO isaearance o$

*iolet color$or&ation o$)ro+n reciitate

The solutionre&ained urle

Fe'l/ The solutionre&ind )ro+nand not all o$ thesa&le dissol*ed

The solution)eca&e darkershade o$ )ro+nand not all o$the sa&ledissol*ed

SA$P%" BS"R/ATINS

Synthesi4edacetylsalicylic acid

All o$ the sa&ledissol*ed and thesolution is tur)id

'o&&ercially#a*aila)leasirin

All o$ the sa&ledissol*ed and thesolution )eca&e $ainturle

'A('U(AT-OS?

Salicylic acid?".=g ':H;O/ 6 &ol SAI /!.; g8 6 &olASAI &ol SA8 6 !=."gI &ol ASA8

".;g

Acetic Acid?0.== &( 'H;=/ 6.=!g AAI &(86 &ol AAI=".g86 &ol ASAI &ol AA8 0.g

Theoretical 2ield?

=.=!! &ol6!=.;gI&ol'EH!O8".;g

C 2ield Actual yieldITheoretical 2ield6".=g o$ the +eighted roductI".;g8 3==:;.;C

-n this e3ercise, the goal +as to roduceacetylsalicylic acid through the organic synthesis$ro& the reaction o$ salicylic acid to aceticanhydride, the starting &aterials. -nstead o$using acetic acid, acetic anhydride +as used assol*ent since the anhydride reacting +ith +aterto $or& acetic acid tends to dri*e the reaction tothe right. -t results $ro& the eli&ination o$ a&olecule o$ +ater $ro& t+o &olecules o$ aceticacid.

i,ure . Structure of Acetic Anhydride

Reference5KL

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