VI.

Results and Discussions

In this experiment the synthesis of acetylsalicylic acid became possible
through the induction of an acetyl functional group into a chemical compound or
simply acetylation. In this particular synthesis, the acetylation used
acetic anhydride as the acetylating agent which readily reacts with the free
hydroxyl group. The mechanism in the acetylation of salicylic acid begin when
hydroxyl group attached in the salicylic acid protonates the α-carbon in the
carbonyl group of the acetic anhydride also known as ethanoic
anhydride" which will eventually yield the acetylated product due to the
displacement of acetate and loss of proton during the reaction.

Figure 11.1

Mechanism for the reaction involved in the synthesis of acetylsalicylic

acid from salicylic acid. Image retrieved
f r o m % http%&&ale#elchem.com&img&aspirin'preparation.gif " The (rest
part of the synthesis was the preparation of the acetylsalicylic acid, in
which ) g of the starting material which is the salicylic acid was
dissolved in a *m+ acetic anhydride and drops of phosphoric acid. The
used of acetic anhydride instead of acetic acid as an acetylating agent in
this synthesis was one of the relevant points in this experiment because the
speed of reaction between salicylic acid and acetic anhydride is faster
compared to the reaction between acetic acid and salicylic acid also the
used of acetic anhydride in the synthesis gives a higher yield compared
with the used of acetic acid. /addition of drops

phosphoric acid in during the experiment was also relevant because it hastens
the dissolving of salicylic acid also it makes acetic anhydride more electrophilic. If
in the case an acetyl chloride was used as an electrophile during the synthesis
addition of phosphoric acid in the reaction will definitely not be needed
because acetyl chloride is electrophilic enough after the mixing dissolving the
salicylic acid with acetic anhydride and phosphoric acid, the mixture then was
sub0ected into heat for about ) minutes. Heating the mixture turned the
heterogeneous white colored mixture into a homogeneous colorless liquid
solution. This observed change in the color of mixture upon heating indicates
that the salicylic acid becomes more soluble or it completely was dissolved due
to the increased in temperature. upon heating the mixture, addition of 4 ml
distilled water followed, in this step a heterogeneous thickened mixture was
observed with presence of slightly formed white precipitate. Thus adding of
water in the mixture upon heating slight formed the desired product
which is the aspirin. The visibility of aspirin upon adding water is due
to the fact that aspirin does not readily dissolve in water. Also, adding water
upon heating the mixture decomposes the excess acetic anhydride used to react
with the salicylic acid. Next upon adding 4 ml distilled water, addition of 46 ml
ice-cold water in the mixture and placing it in an ice-bath further made the
desired product aspirin more visibly formed. Upon cooling the mixture, suction
filtration comes next, in which white powdered substance was obtained during
isolation. After suction filtration the precipitate in the filter paper was
allowed to dry using a steam bath and after drying some traces of small
bits of sugar like crystalline solids became visible.Next part of the experiment was
the puri(cation of the crude product&aspirinobtained during the preparation of
acetylsalicylic acid from salicylic acid or simplythe recrystalli7ation of the aspirin.
To start with the recrystalli7ation process, 6. gof crude aspirin from a total of
6. 8 g of crude product obtained during thepreparation of acetylsalicylic
acid was allowed to dissol#e in a 8 ethanoldropwise until all the crude
aspirin completely dissol#es./fter completely dissol#ing the crude aspirin,
addition of cold distilled waterdropwise follows and then the mixture was
allowed to cool in an ice bath both thisstep ga#e an obser#able reappearance of
sugar li!e crystals which was (rstobser#ed during the preparation of acetylsalicylic
acid. /fter the obser#edreappearance of the desired recrystalli7ed&puri(ed
aspirin suction (ltration follows
and in this step more #isible crystals left in the (lter paper was
obser#ed. 3ponsuction (ltration the (lter paper together with the more #isible
crystals was againallowed to dry under the steam bath and after drying much
more #isible (necrystals was obser#ed./spirin was recrystalli7ed in this
experiment using 8 ethanol and not withhot water because !nowing that
aspirin undergoes reactions as of esters once hotwater was used during the
recrystalli7ation there would be a great tendency thatthe aspirin will be
hydrolysed and may yield bac! into carboxylic acid./fter the preparation of
acetylsalicylic acid, recrystalli7ing&purifying the crudeaspirin the last part of the
synthesis was the characteri7ation of aspirin or simplydistinguishing the
di9erences between a pure salicylic acid, commerciali7edacetylsalicylic acid :
the laboratory synthesi7ed acetylsalicylic acid using
#ariouscharacteri7ation tests. Three #arious tests namely, ;e<l
*
test which tests thepresence of impurities speci(cally the presence of
unreacted salicylic acid in thesynthesi7ed aspirin, =$n>
?
test which detects the presence of )@ alcohols, 4@alcohols and phenols in the
compounds and lastly the Atarch test which utili7ed anI
4
&=I solution or simply iodine solution to detect the presence of starch in
betweenthe commercial and synthesi7ed aspirin. In the ;e<l
*
test only the synthesi7edaspirin yields a positi#e result in which the mixture
turned into a bright purplesolution which indicated that the synthesi7ed
aspirin still contains unreactedsalicylic acid in this case, we must consider
using more amount of excess aceticanhydride to completely utili7ed the
limiting reagent which is the salicylic acid. 5exttest was the =$n>
?
test, in this particular test only the salicylic acid again yieldsinto a positi#e
result because in its structure it contains a ben7ene ring withattached >1 group
or simply the sturucture of phenol. +ast characteri7ation testconducted was the
Atarch test in which the commercial aspirin yield a positi#eresult because it
contains starch in its composition./s for the 2uantitati#e analysis in this
experiment the percent yield of thecrude aspirin was B .* in which
the acetylated ).6 g of salicylic acid only yields to6. 8 g of crude aspirin
somehow far from the theoretical yield which was ).*6? g ofcrude aspirin
supposedly. This discrepancy in the percent yield may be attributed tothe
incomplete acetylation of salicylic acid by acetic anhydride thus much
moreexcess reagent must be used to completely consume the limiting reagent
which isthe salicylic acid to ha#e a higher yield of the desired product. /nd for the
percent

reco#ery of the crude aspirin it yielded . pure aspirin meaning that

thesynthesi7ed aspirin was almost pure but not perfectly pure this may because
of theexperimental error occur during weighing, (ltration improper washing of
crystals,using warm&hot sol#ent in washing& rapid crystalli7ation which may
trapped someimpurities", transfer, drying and other un!nown factor that greatly
a9ects the purityof the aspirin/nd lastly for the melting point determination of
the crude and recrystalli7edaspirin, the crude aspirin got a $C range
)64@<-)6?@<" and for the synthesi7edaspirin it got a $C range ))4@<-
)*8@<". <ompared with the literature #alue of the$C of a pure aspirin which is
)*B@<, the $C range of the crude aspirin seems #eryfar this may be due to
presence of some impurities during the (rst part of theexperiment speci(cally the
presence of unreacted salicylic acid and for thesynthesi7ed aspirin though it has
the literature #alue of the $C of pure aspirin it isstill not enough to conclude that
the synthesi7ed aspirin is pure enough because the$C range of synthesi7ed
aspirin is 2uite wide meaning it might ha#e loose, une#enpac!ing of
crystals resulting in the wide $C range.VII. Aummary and <onclusion/s for the
summary, the synthesis was of acetylsalicylic acid from acommercially a#ailable
compound which is salicylic acid was indeed a usefulprocess in organic
chemistry. Through simple preparation of acetylsalicylic acid byacetylation of
salicylic acid, and recrystalli7ation a much more safer and usefulorganic
compound was obtained from a highly strong compound which is salicylicacid.In
this experiment, a successfully synthesi7ed aspirin was obtained yet it maynot be
useful enough because of some impurities that is present in the compound.VIII.
References$oore, illiam.
Laboratory Manual for Organic Chemistry: A Microscale Approach.
5ew Eor!%$cFraw-1ill, c)88B. Crint. Gones Het al. .
Laboratory Manual to accompany World of Chemistry: ExtendedVersion.
>rlando, ;lorida% Aanders <ollege Cublishing, c)88). Crint.A7afran, Jsi.
Microscale general chemistry laboratory : ith selected
macroscaleexperiments.
5ew Eor!% iley : Aons, Inc.,c)88*. Crint.

Di#ision of >rganic <hemistry and 5atural Croducts.

Laboratory Manualfor a coursei n ! a s i c O r g a n i c C h e m i
stry "Chem #$.%&.
Institute of <hemistry, <ollege of /rtsa n d A c i e n c e s , 3 n i # e r s i t y
of the Chilippines +os KaLos, <ollege, +aguna%
5 i n t h Crinting, c46)*. Crint.1enric!son Het al. .
A Laboratory for general' organic' and biochemistry.
th ed. 5ew Eor!, 3A/% $cFraw-1ill,c466M. CrintIN. Remar!s and
Recommendations/ much more useful and safe aspirin might be synthesi7ed
during thisexperiment if the Institute of <hemistry may ha#e pro#ide a much
more cleanlaboratory materials, much precise and accurate laboratory
e2uipments and suchmaterials needed in a full synthesis of aspirin