S. Y.8.

PHA RM(St-: M-JII) Pharmac eutical Organic Chemis try-II

').6 \ t>i \ 'l..04..'i

Experi ment No : q

Aim: To synthes ize benz.anilide from aniline by l3enzoylation reaclion.

Reference:
June
1. Labora tory Manual of Organic Chemis try by Raj . K. Bansal, publish ed on
1983,Page No-111
2. Practical Organi c Chemis try by Frederi ck George Mann and Bernard Charles Saunde rs
.
Publish ed by Longan Inc.,Fou rth Edition ; Publish ed on 1 January 2009, Page No-245
ed by
3. College Practical Chemistry by V K Ahluwa lia, Sunita Dhingr a; Publish
Univers ities Press( India) Private Limited 2005; Page No-235 .
Requirements:
l.Chem icals: Aniline - 2ml, benzoyl chloride-3ml, cold water and hot alcohol.
2.Instr ument: Weight ing balance, melting point apparatus and Hot air oven.

3.Appa ratus: Conical tlask-25 0 ml, Buchne r funnel, Measur ing cylinde r, Filter paper.
Proced ure:
Place 2.6g (2.5ml ) of aniline 25 ml 10% aq NaOH solution in 75-100 ml conical flask,
Heat is
then add 4.3g (3.5ml ) benzoy l chlorid e slowly with vigorou s shaking for l 0min.
the
evolve d in the reaction. The crude benzoyl derivative separates as a white powder. When
smell
reactio n is comple te (i.e., when the odour of benzoyl can no longer be detecte d:
Filter
cautiou sly), make sure that the reaction mixture is alkaline and dilute with 10ml of water.
filter ( if
off the produc t with suction on a small Duchne r funnel, break up the mass on the
necessary), wash well with water, and drain. Recrystallization from hot alcohol (or methyl ated
spirit); filter the hot solutio n through a hot water funnel or through a warm Buchne r funnel.
the Practic al
Collec t the crystal s which separat es and dry in the air or in the steam oven. Report
yield, % yield, melting point of the produc t.
 t
t
S.\'.B. PHARMACY Sem-111
Pharmaceutical Or anic Chemislr -II ••
Experiment No. 10
Date:- ~\o~)'l..Oll.j
I
Aim: To Synthesbe Phenyl Ben:zoate from Phenol and Bcnzoyl Chloride by BenlOylaUon.
Rcferentt:

I) Vogel A. I; Elementary Practical Organic Chemistry: Part I, Small Scale Preparations;

d
2" edition, CBS publication.Pg. No.

2)Fumiss B.S., Hannaford A.J., Smith P. W.G., TatcheJI A.R, Vogel 's Textbook of

Practical Organic Chemistry; 5th edition, Pearson publication, Pg. No.

3)The Merck Tndex: An encyclopedia of chemicals, drugs and biologicals, L3'h edition, Merck

Research Laboratories Division of Merck & Co. Inc, Whitehouse Station, N .J .,200 I, Pg. No.

Chemicals: - Phenol, Bcnzoyl Chloride, Sodium Hydroxide, Methylated spirit, etc.

Apparatus: - 250ml Round Bo1tlc Flasks, Beakers, Reflux Condenser, Buchner flasks,

Buchner Funnel, thennometer, etc.

Equipment's: - Stand, ThieJes tube. Tripod stand, burner, etc.

Procedure: -

1- In a IOOmJ conical flask dissolve 2.5 gram of phenol in 35 ml of 10% sodiwn hydroxide
solution and add 5 ml benzoyl chloride.

2- Cork the flask properly and Shake /

the mixture until the smeJJ of benz.oyl chloride dis/ppeared.

3- The phenyl benzoate which separate iB"' filtered off wa5hcd with cold water urieu and
recrystallized from alcohol
 S.V.B. Pharmacy (SEM- llf)

Experiment No. ' \

Alm: To Synthesis of acetanilide from aniline.
S ders
Reference : . , . d Bernard Charles aun
1) . Practical Organic Chemistry by Frcdenck George Munn
an
Publi~hed by longan Inc, Fou11h Edition; Page No I 08.
2) Edition CBS publication ,Pg_No. . . . p t I Small scale Prep arati on;
3) Vogel A.I; Elementary Practical Orga111c Chem istry. ar ~

Requ irem ents :

Chemicals : Acetic acid/anhydride mixt ure-2 0 ml
Aniline - JO ml

Apparatus : Conical flask - 250 mI

Reflux water-condenser set
Buchner Funnel
Measuring cylinder
Filtre paper
oven.
Equipment: Weighing balance, melting point apparatus and hot a.fr
Proc edur e:

Add 20 mJ of a mixture of acetic anhydride and glacial

aceti c acid (equa l volu mes) to 10 ml (10.3
denser to the flask and gently boil
g) of aniline in a conical flask of 250 mJ. Fit a reflux water-con
ml of cold wate r with cons tant stirri ng.
the mixt ure for IO min. Then pour the hot liquid into 200
and wash the crndc acetanilide well
The acetanilide quickly crystallises. Filter yield by a pump
volume of acetic ucid and two
with water. Recrystallise from about 60 ml of a mixture of one
, again wash thoroughly with water
volumes of water: fiJter off the colourless crystals at the pump
drain
 S.Y.B. Ph
•trnacy (SEM-IU)
Experiment N Ph arm ac eu tic al Or
ga nic Ch cm i.,try-11
o. 'l
Ahn: To P~ ar e ,,
.
...,, 4, 6-tnbromoarul. tne
. Date: - 1o \ l> ~ \
from aniline.
Reference · I v
· · oge1,s "'I extbook
of Practi.cal
Organic Chemistry by
J. Hannaford, Peter W Brian S. Furniss. Anton
. G. Smith & Austin R. y
2 Tatchell ; Fifth Edition; Page No .- 90
· Mann F. G., Saunde 9.
rs B. C., Practical Orga
nd
r ia nic Chem istry, 4th Edition, Darling Kindersly
Pvt. Ltd., New Delhi,
3. Comprehensive Prac Pa ge No .
tical Organic Chemistry: 165.
K. Ah luwalia, R. Agga Preparation and Quantitative Analysis By
rwal; Page No. t 08. V.
Requirements:

Chemicals: Aniline, Br
omine, Dilute hydrochlor
ic acid, Rectified spirit.
Apparatus: Beaker,
Filtration set etc.

Equipment's: Stand,
Thieles tube, Tripod stand, Burner, etc
.
Procedure: Dissolve
IO g (5 ml taken) of an
iline in 40 g (20 ml tak
and stir well with a me en) of glacial acetic ac
chanical stirrer while id
running in slowly a so
taken) of bromine in 34 lution of 52.8 g (8.4 ml
ml (20 ml taken) of gla
cial acetic acid. The be
ice during the addition aker should be cooled
as the reaction is exoth in
ermic. The final produ
yellow by the addition ct should be coloured
of a little more bromine
if necessary. Pour into
the pump, wash well wi excess of water, filter
th water, press thorou at
ghly and dry. The yield
J J9-1206 C, is quantita oftribromoaniline , m.
tive. Recrystallise a sm p.
all portion from indus
trial spirit.

DR.I>.)'. PATIL COLLEG

E OF PHARMACY
\~ • Chemistry - II
Pharmaceutic-al Org:rn1c

\~ s. y. B ,Pbarmacy(SEM-111)
\ \}
I~,
j
Experiment No: I 9.-

r m characteriz ation or the

,~
I .:. Aim: To synthesize p-bromoace
tanllide frotn acetanilide and per or

1~ product.

' ~-3 Reference:

1) Vogel A. L. ; Elementary Practical Organic Chemistry: Pa

.
'
. ..
rt 1 Small Scale Preparabons; ed1t1on,
CBS

publication, Pg. No.

,;>
. . "A Modem Approach, 2nd edition, Published by
~ 2) S. K. Ghosh, Advanced General Orgaruc Chemistry,
new central book agency (p) Ltd., Pg. No.
~
3) The Merck Index: An encyclopedia of chemicals, drugs and b10. l . l 13 edition Merck Research
~ ogtca s, '
Laboratories Division of Merck & Co. lnc, Whitehouse Station, NJ.,200l,Pg.No.
~

3 Requirements : .... .

Apparatus: Conical flask. Funnel, Beaker, Filter paper, Burctte etc.

Instrument: Weighing Balance, Melting point apparatus and Hot air oven.

Chemicals: Glacial acetic acid (70 ml), Bromine(4.2 ml), Sodium bisulphite, Rectified spirit,
Acetanilide( 10 g).

Procedure: Dissolve 7.0 gm of finely powdered acetanilide in 25ml of glacial acetic acid in a 250 ml
conical flask. In another small flask dissolve 8.5 gm. (2.7ml.) of bromine in 12.S ml of glacial acetic acid,
and transfer the solution ofburette or a small separator funnel supported over the nask. Add the bromine
solution slowly and with constant shaking to ensure thorough mixing: stand the flask in cold water. When
all the bromine has been added, the solution will have an orange colour due to the slight excess of bromine;
a part of the reaction product may crystallize out. Al\ow the final reaction mixture to stand at room
temperature for 15 min with occasional shaking. Pour the reaction product into 200 ml of water, and rinse
the flask with about 50 ml of water. Stir the mixture well and if it is appreciably coloured, add just
sufficient sodiwn bisulphite solution to remove the orange colour. Filter off the crystalline precipitate with

DR.D.Y.PATIL COLLEG E OF PHARi'1ACY,AKRUDI.PUNE-41044 PAGf

S.Y.B. Pharmacy (Sem-l ll) Pharmaceutical organic chemistry-11

Experiment No. - I~
Date: l .'·\ \ o9 \ '.l. O l..~

Alm: Synthesis of 5-nltrosaUcylic acid from salicylic add.

Reference: l) Experimental Organic Chemistry by Sonia Ratnan

i and Shriniwas Gurjar
Published by PHI Learning Private Limited, Delhi
2012; Page No. 104,
2) Microscale Organic Laboratory with Multistcp and Multiscalc Synthe
ses by Dana W. Mayo,
Ronald M. Pike and David C. Forbes Published by John Wiley & Sons
Inc.; Fifth Edition Page
No. 379

Requirements:

1) Chemicals: Salicylic acid, Acetic acid, Calcium nitrate tetrahydrate.

2) Apparatus: Conical flask, Funnel, Beaker, Filter paper.'

Procedure:

3 g of calciumnitrate tetrahydrate is dissolved in \ 0 m\ of acetic

acid within a \ 00
ml conical flask by gently heating on a water bath. 2 g of salicylic acid
is added and the reaction
mixture is heated on a boiling water bath (below 80°C) for few minutes.
A dark red solution is
fonned . Then the dark- red coloured reaction mixture is poured into a \ 00 m\
20 beaker contain ing
ml ICC
cold
water.
A turbid dark red coloured solution fonns which is kept in a refrigerator and
after 4-5 hours
yeUow crystals of 4-Nitrosalicylic acid separates out The crude product
is filtered at the suction
pump, washed with cold water and dried. Ycllow precipitate of 4-Nitr osalicy
\ic acid is obtained
with yield of 1.32 g, m.p. 23
 S Y.8 .PHARMtSEM-lll )
Ph(mnoccut1ca l Or§.?ni ~ ~ nistry;ll

Experiment No: l 5

Aim: To synthesis Acetyl solicylic acid (Aspirin) from salicylic acid.

Rcferen ~:

J. Vogers text book of Practical Organic C hemistry, Page No. 1290.

2. Practical Organic Ch~mist ry by Frederic k George Mann and Bernard Charles

Saunder s
Publishe d by Longan lnc., Fourth Edition; Page No. 110.

3.

Requirements:

Chemic als: Salicylic acid - 6 g, Acetic anhydri de - 8.5 ml, Concen trated 1-12S04
- 3-4
drops, Methyla ted spirit

Appara tus: Conical flask-2 50 ml, Buchner funnel, Glass rod, Beaker, Filter paper.

Equipment: Weighing balance, melting point apparatus, hot air oven.

Procedure: Weigh 6 gs of salicylic acid and transfer it to a clean and dry 250 ml conical
flask. Add 8.5 ml acetic anhydri de and 3-4 drops of concentr ated sulphuri c acid to
the flask
carefully and mix thoroug hly. Warm the mixture on water bath at 60 degrees about 20 min
with frequent stirring. Allow the contents in the flask to cool and pour into I00 mI cold water
in 250 ml beak.er with constant Stirring. Filter the crude product on a Buchner funnel using
suction, wash with cold water. Recrysta llize from boiling water along with small quantiti es of
methylated spirit. Dry the synthesized product in an oven at 90 °C and calc ulate the yield .
 f
f
t
Pharmaceutical Organic Chemistry-II _ ~
Expe • C,
runent No: , 6
Date: ;?, I\ o Q) '.1 0~ '-i
Aim: To pre (:
pare benzoic acid from alkyl benzoate by Hydrolysis reaction.
Refercncc:

I.College Practical Che .

Publ' I mistry by V K Ahluwalia, 'iunita Dhingra and Adarsh Gulati.
ts led by Univ ..
crsittes Press (India) Private Limited 2005, Page No. 255
2.

3.

Requirements:

Chemicals: Ethyl bcnzoate- 2 ml. Sodium hydroxide solution I0% - 15 ml, Hydrochloric
acid sufficienL

Apparatus: Round bottomed flask, Reflux condenser, Funnel, Measuring cylinder, Beaker.

Equipment: Weighing balance, melting point apparatus, hot air oven.

Procedure: A mixture of ethyl benzoate (2 ml) and sodium hydroxide solution ( 1S ml, 10%)
is refluxed in a round bottomed flask fitted with a water condenser on a water balh (temp. 90-
100 oC) for about 30 minutes till the ester layer disappears. Then the solution is cooled and
acidified with HCI. The resultant acidified solution is cooled in an ice bath. The separated
benzoic acid precipitate is filtered and recrystallised from hot water.

Molecular fonnula of ethyl benzoate = C9HI 002

Molecular fonnula ofbenzoic acid= C7Il6O2

Weight of ethyl benzoate = I 50 g/mole

Weight ofbenzoic acid= I 12 g/rnole

DR.D. Y.PA TJL COLLEGE OF PHARMACY, AKURDI, PUN FA 11044

 l'lu1111u11·1•11tlrnl ()1 ),!t1 llk C'h1·111l,h) 11,

l ,,,~, illl\'111 N,,. II ll11ll': <1 l11 C\ \ 'l OJ \\

,,~~
\~

l"~ \) 1in.'f11 t hc111i,t1) 1:111111,1111w11tt1II) \k11i1111 Rr:1di 1

l'ubh~hcd b) Anc lh'-.1\..~ P,1 l 111 Fir:.1 hlitillll, P,111c
111 hy V 1-.. /\hht\\ ;Iii.,:

13 2)
N11. I~'!

\ -.)
3)
~

~
Req11irtmcn~:
~
Chemicals: Methyl Salic) late 3ml, Sullitric Acid l6~
I), Sodium I I~ lln.1:\iJc to~ 1)

Apparatus: 200ml Beaker, 115ml Erlenmeyer Fins\..,

FillrM ion /\pprntus,'2001111 rcl1ux
Apparatus

Instrument: Weighting b:ilance, melting point nppnrn

tus nnd Hot uir o,cn.
Procedure: 3 ml mcthyl-sulic)latc (density- 1.18-1
) is 1nk~n in to u 200 ml RRF. 50
ml of 61\1 NnOH solution isaddcd 10 ii with II coupk
or boiling chips. The s11lution is
refluxed for 30-45 minutes from the point the mi11.1u
rc ~,o,1s to boil. If the rtnction
mi:\ture still has oil or is cloudy, continued to reflux
. Once the mixture is clear nnd
homogeneous, tl1cn the solution is checked \\hcther
ii no loniicr hu, ing ~mdl of oil
of wintergreen . If the smell still c:-.ists, then contin
ued to rcllu:\ for some more
minutes. Boilini chips are remo\'cd a11d lhc solulio
n is transferred to n '.!.50 ml
beaker. A 61\1 I hSO~ or h)drochloric acid is uJJcJ
slo" ly wi1h s1irring until the pl I
is 2.0. 111c mix solution is cooled in ill\ icc-bnlh for 10 minutes,
,acuum liltcrcd :ind
rinsed "'ith ice cold "utcr. The producl is recrystallize
d from h11t water: ) icld l.'.! g
m.p.158-159°.

DR.D.Y. PATIL COLLEGE OF PHARMACY,

AKURDI, l'UNE-41044
 . orga nic Chemistry-II
Phar11111ceut1cal
S.Y.U.PllARM (SEM Ill)

Date: 11,\09 \ l Y
Experiment No : I 9

Aim: To synthe~ize \-phcnylazo-2-napthol from aniline.

Rtference : . . Ch
l.Mann , F.G Saunders, D.C., "Pracl1cal Organic em1·stry" 41h Edition (Reprint I978)
,
d 20
Longman Group Ltd., Lon on, 11 ' Page no.210-211.
. .
1. Kar A. Advanced Practical Mcd1c . New Age International (P) L'1m·1
1ed
mal Chemi stry,
Publication, New Delhi, 2007, Page no.136·

3
~
Requirements:
I ~ I.Chemicals: Aniline-4gm/3 .92ml, Conc.HCl-12.Sml, . . I Sodium
D1st11led water-l 2.8m •
I
'I'~ nitrite-3.2gm . p..napthol-6.24gm, NaOH-40m\.

2.lnstruments: Weighing balance,Hot air oven, Melting

point apparatus.

1~ 3.Apparatus: Two beaker-250ml, Glass rod, Inverted

glass stoppe r.
13
13 Procedure: Solution A: This solution is prepared by adding
conc.HCI and dilute with 12.8ml distilled water. Beaker
4gm/3.92ml of aniline in 12.8ml
is kept in an ice bath with frequent
tJ stirring till it attains a temperature between 0-5°C.
Solution 8 : In another beaker, dissolve 3.2gm sodium nitrite
1~ same ice bath.
in 15ml water and keep in the

~ Add the solution A&B together, this will give solution C.

Place a drop of sodium nitrite solution
3 on KI-starch paper that will tum blue in presence or nitrou
s acid. Next, dissolve 6.24gm of P-
naptho\ seperatcly in 40ml ofNaOH solution, and cool the
~ naptho\ solution in an ice bath (0-
s•q.
~ Add the cold diazonium salt solution to the jl-napthol solutio
n with constant stirring and not
w allowing temperature of reaction to rise beyond 5°C. Allow
the mixture to stand for 30-40min
with stirring so as to complete the reaction.

"''3
DR.D.Y.PATIL COLLEGE OF PHARMACY, AKUR
DI ,PUNE-411044
 Aim : To prepare benzll from benzoln.

Reference: I) Vogel's Textbook of Practical Organic Chemistry by Brian S. Furniss, Antony

J . Hannaford, Peter W. G. Smith & Austin R. Tatchell; Fifth Edition; Page No.- 1045

2) Practical in organic chemistry, by Hitesh G. Raval, Sunil L. Baldania and Dimal A. Shah,
Nirav Prakashan, Page no: - 273

Requirements:

Chemicals: Benzoin,

cone. HN03,

Ethanol etc.

Apparatus: Round bottom flask, Beaker, Pipette, Glass rod, Buchner funnel etc.

Procedure: 20 g of benzoin and 100 ml of concentrated nitric acid are taken in a round
bottomed flask and heated on a boiling water bath for about 1.5 hour with occasional
shaking until the evolution of oxides of nitrogen ceases. The content is poured into 300 -
400 ml ice cold water with shaking. Then the product is filtered with suction and
washed with cold water. It is recrystallized from ethanol, taking 2.5 ml per gram; m.p.
94-96 oC.
 EXPERIMENT NO: 1~ DATE: ..l.O \ 0~ \ '.l.Y

Aim : To prepare dibenzal acetone from benzaldehyde

. K . Mann F · G ·,
Reference: s aund ers 8 . C., Practical
. . Chemistry 4th Edition
Organic
D o rl 1ng 1ndersley. ' ·

Requirement:

~tJ~~~~~Z;7J:'i~~b~~-21z,~1 Acetone -4 ml Methylated spirit -10 ml 10% aqueous

Apparatus: Conical flask or wide mouthed bottle, Beaker, Measuring cylinder Buchner
funnel.etc. '

Procedure:
About 10 ml (10.4 gm) of benzaldehyde and 4 ml of pure acetone is thoroughly
mixed with 10 ml of methylated spirit in a conical flask or wide mouthed bottle. 2 ml of
10% aqueous sodium hydroxide solution is diluted with 8 ml of water, and this dilute
alkali solution is added to the former solution. The mixture is shaken vigorously in the
securely corked flask for about 10 minutes (releasing the pressure from time to time if
necessary) and then allowed to stand for 30 minutes, with occasional shaking and
finally cooled in ice-water for a few minutes. During the shaking , the dibenzyl-aceton_e
separates at first as a fine emulsion which then .ra~idly forms pale yellow crystals. It 1s
filtered at the pump, washed well with water to eliminate traces of funnel ,etc.
 em istr y-I I
Ph •r~ ace utj cal Or gan ic Ch
S..Y.B . Pha rm acy (SEM"..JJJ)

Experiment No . 1 \

d from p-aminobenzoic acid

Alm: To synthesizep-iodobenzoicaci
s,A nto ny
ctic al Org ani c Ch em istr y by Bri an S. Fur nis
Reference: 1. Vo gel 's Tex tbo ok of Pra .- 909 .
, Pet erW . G. Sm ith& Au stin R. Tatchell; Fifth Editjon;Page No
J. Hannaf ord th , Do rlin g Kin der sly
2. Ma nn F. G., Sau nde rs B. C., Pra
ctical Org ani c Che mis try, 4 Edi tion
. - 165.
India Pv t Ltd., New Delhi, Page No Pre par atio n and Qu ant itat ive An aly sis
By V.
ctic al Org ani c Che mis try:
3. Co mp reh ens ive Pra
108.
K. Ahluwalia, R. Aggarwal; Page No.
Requirements:
ide,
Hy dro chl oric aci d, Sod ium nitrate, Pot ass ium iod
Cbemlcals: p-a min o ben zoi c aci d,
e or anhydrous magnesium sulphate.
Sodium hydroxide, Calcium chlorid
h vessel,
ara tus : Ro und Bo ttom ed Fla sks , Beakers, Conical Flasks, Water bat
App
cylinder, Pipette, Stirrer, etc.
Reagent bottles, Funnel, Measuring
, Melting poi nt app ara tus and
Hot air Ove n
Equipments: Weighing balance
ml of3 M
benzoic acid in a 250 ml of rou nd bot tom flask. Add l 0
Procedure: Pla ce JO ml of p-a min o perly.
flask. Wa nn gen tly whi le stir ring unt il reaction mixture is dissolves pro
HCI in RB tions in ice bat hs until
aNO z in 10 ml wat er in a 100 ml of beaker. Cool bot h solu
Dissolve 10 gm ofN p below 10 °C. Test with
5 °C. Ad d sod ium nitr ite solution to round bottom flask, kee
bot h are bel ow e 15 ml of KI in 100 ml
pap er, add min ute am oun ts of ure a to giv e a neg ativ e test . Dis solv
star ch- iod ide solu tion , stir..Heat gently,
bea ker . Pou r dia zon ium salt into SOO ml beaker with the KI
wa t« ill ano the c water.
of gla ss rod . Col lect pro duc t with vacuum filtration, wash wit h a cold
pop foam with stir ring
-/4 water. Ob tain ed crude product.
.R.o ciy stal liu wit h 80% cthanol/20
 aq HCI
NH 2 !
,
~
Mcchanbm .
c, 0
, ~1
0c1 N
H~HCOOH Ci\u-11
HCI <Jij ,:
u~ ~COOH N COO I
2-Aminob<!nzoic
acid
~ ~v aN01 )vcooH
NaCl+ 2 H:tO

IK
~~
~'
.;
Na+ KCI '2-lod
obenzoi<:
ac id
.. ,,,.
~
Calculation:
~ U.t u 1 0 J ~ t- · 0 ~-
p
~y \
fl - 0-M£ C"\O c:: t--1.0 I C c...uJ C t- 0 p
p~ c c.lt 'c!.r :cf{
u l..l.)
r
'?, c.I'l LO C. a c)' cl ..
,._ ~
Q __ {. X O ,
1 1 1 ,> \l ! C ~ l\ t 0
0I
Cl rut.Kc. cJ
'I~ u
\0 t.. x,, x c . \£- 0 oQ ___ .., ,f fi C.
Q -re'-/-..
c.\ c.. ~f~
e
~ ~ d.
0/
o Y f' o <'> c:. 1 C;
" " C\ c
\&> .. 0£
DR.D.Y. PATIL COLLEGE OF
PHARM
e
A C..'Y, AKURDI, "PUNE-41104
4
~
',~