HoshMuhammadLashar

i,Depar
tmentofPhar
macognosy
,Facul
tyofPhar
macy
,U.
O.SJamshor
o

Cl
ass:
Final
Prof
.Phar
m.D.Cour
seNo:
Phar
m:719Subj
ect
:Medi
cinal
Chemi
str
y(Lab)
Obj
ect
:Sy
nthesi
sofaspi
ri
ncr
yst
alsandest
imat
ionofi
tsper
cent
agey
iel
d

Requir
ements
Chemical
sSal i
cyl
icaci
d,aceti
canhy dri
de,sulf
uri
cacidanddoubl
edist
il
ledwater
.
GlasswaresErlenmeyerfl
ask(50-100mL) .Beaker
s(100-200mL),measur
ingcyli
nder
,
test
-t
ubes,spatul
a,gl
assrod,dropperandf i
lt
erpaper.
Accessor
iesAnalyti
calbal
ance,hotplate,
steam bathandicebat
h.

Theor
y
 Acetylsali
cyli
caci d,commonl yknownasaspi rin,isthemostwi delyuseddr ugin
thewor ldtoday.Itsanal gesi c, anti
pyretic,
andant i-
infl
ammat orypr operti
esmake
i
ta power fuland ef fect iv
e dr ug t or eli
v e sy mptoms ofpai n,fev er,and
i
nflammat i
on.
 Sali
cylicacid,whosenamecomesf r
om Sal ix,thewi l
l
ow f ami lyofpl ants,was
deriv
edf rom wi l
low bar kext racts.Hi ppocratest heanci entGr eekphy sician,as
wellasNat i
veAmer icans,pr eparedwi l
lowbar kt easasheadacher emedi esand
othertonics.Inmoder nt i
mes, sal
icyl
icaci disadmi ni
steredint hef orm ofaspi ri
n
whichi slessirr
it
at i
ngt ot hest omacht hansalicyli
cacid.
 Aspiri
ncanbesy nthesizedbyr eactingsal i
cy l
icaci dwi thacet i
caci di nt he
presenceofanaci dcat alyst.Thephenolgr oupont hesal icylicacidf ormsan
esterwi t
ht hecar boxy lgroupont heacet i
caci d.Howev er,thisr eacti
oni ssl ow
andhasar elat
ivelylow y ield.I faceti
canhy dridei susedi nsteadofacet i
caci d,
thereact i
oni smuchf asterandhasahi ghery i
eld.Ther eactionsar eshowni n
fi
gure1. 1and1. 2r espect i
v ely.

Fi
gur
e1.
1Sy
nthesi
sofacet
ylsal
i
cyl
i
caci
dbyr
eact
ingsal
i
cyl
i
caci
dwi
thacet
icaci
d

Bat
ch2k20
 HoshMuhammadLashar
i,Depar
tmentofPhar
macognosy
,Facul
tyofPhar
macy
,U.
O.SJamshor
o

Fi
gure 1.2 Sy nt
hesis ofacetyl
sal
icyl
i
c aci
d by reacti
ng sali
cyli
c acid with aceti
c
anhydr
ide
 Aspi r
inisnotv erysol
ubleinwatersotheaspiri
nproductwi llpreci
pit
atewhen
wat erisadded.Someoft heothercompounds,aceti
canhy dr
ideandacet icacid,
dissolveinwater.Butsali
cyl
i
cacidisonl
yslight
lysolubl
eincol dwater.Vacuum
fil
tr
ationwi l
lseparatethecryst
all
i
neaspiri
nawayf rom everythi
ngel seinthe
reactionmixtur
eexceptforanysali
cyl
i
cacidthatdidnotreact.

Pr
ocedur
e
 Pl
ace1gofsal
i
cyl
i
caci
dina125mLEr
lenmey
erf
lask.

 Add3mLofaceticanhydr
ide;fol
l
owedby3-
4dr
opsofconc.H2SO4 (
usea
dr
opper
,H2SO4i
shighl
ycorrosi
ve).

 Heatt
hef
laskgent
lyont
hest
eam bat
hforatl
east10-
15mi
nut
es.

 Duringheat i
ngputatl east60mLofdi st ill
edwat erintoa150mLbeaker( or
similarsize).Thenputt hisbeakeri nani ce-wat erbat h.Uset hiscoldwat erfor
thef ormat i
onaspi rincr ystals.
 Aftert hereactionhasgoneonf or10- 15mi nut es,Tur nof ft hehotpl ateand
carefullyremov ether eactionf laskf rom t hewat erbat h.
 Add1- 2mLofdi sti
ll
edwat ert ot hef lask.Thi swat erwi llreactwi t
hany
excessacet i
canhy dri
de,conv ertingi tt oacet icaci d.Keept hemi xtureunder
thehoodatr oom t emper aturef oraf ew mor emi nut es,someoft heacet i
c
acidt hatisproducedatt hisst epwi llvapor i
ze, andt hev apori sirri
tat
ing.
 Add8- 10mLofchi l
ledwat ertot hef l
askandswi rlitaroundt omi xit.Ast he
fl
askcool s,crystalsofaspi ri
nwi llstar tt of orm.Wheny ouseecr y
stals,put
thef l
aski nani cebat hfor10mi nut es.( Aspi ri
n, l
ikemanyot hersubst ances, i
s
mor esol ublei nhotwat ert hani ncol dwat er.Ther ef or
e,t omaxi mizet he
amountofcr ystals,itisbestt ocoolt hemi xtureasmuchaspossi ble.
)Ifno
crystalsappear ,gent lyscr atcht hei nsideoft hef l
askwi thast ir
ringrod.
 Collecttheaspi ri
ncr ystalsbyv acuum f il
t rati
on.

 Whentheproducti
scompl
etel
ydr
y,wei
ght
hepr
oductandcal
cul
atet
he
per
cent
agey
ield.

Bat
ch2k20
 HoshMuhammadLashar
i,Depar
tmentofPhar
macognosy
,Facul
tyofPhar
macy
,U.
O.SJamshor
o

Saf
etyPrecaut
ions
 Acet i
canhydri
dei sir
rit
ati
ngtothenoseandsi
nuses.Keept
hiscompoundunder
thehoodatallti
mes, andavoi
dbreat
hingt
hevapor
s.
 Theaspi ri
nthaty oumakei nthi
slabisNOTpureenoughtobet akeni
nter
nal
l
y!
Donotingesttheaspiri
n.

Result
s
Table1.1r
esul
tsfr
om thecl
ass
Group# Theoret
ical Act
ual
yiel
d %y
iel
d
yi
eld

Di
scussi
on:
Sel
f-
expl
anat
ory

Sour
cesofer
ror
:Sel
f-
expl
anat
ory

Ref
erences:
1.JamesChi ckos,Dav idGar in,andVal er i
anD' Souza.Uni versi
tyofMi ssouri
–St
.
Louis;Chemi stry)
2.ht t
ps://l
aney .
edu/ chel i
-f
ossum/ wp- cont ent/uploads/sit
es/ 210/2012/01/ 8-
Synthesis-of-Aspi r
in.pdf
3.ht t
ps://www2. chem21l abs.com/ l
abf il
es/ uofc_glaspiri
n_lab.pdf
4.A. HBecket t,J.Bst enlake,Practi
cal phar maceut icalchemi stry4thedi
, t
ionparttwo
2004, Asiapr intographshahdar aDel hi.
5.Ev ans,W. C. ,Tr easeandEv ansPhar macognosy .6ed.2009:Edi nburghLondon
New
YorkPhiladelphi aStLouisSydney Toront o.htt
p://downl oadsphar macy.blogspot.
co
m/ 2011/01/ phar macognosy -by-
treese- and-evans_ 4513.html .

Bat
ch2k20
HoshMuhammadLashar
i,Depar
tmentofPhar
macognosy
,Facul
tyofPhar
macy
,U.
O.SJamshor
o

Bat
ch2k20