PG Department of Chemistry_MSc-II Sem-IV_Organie Chemistry Practical Lab-yII

Aim: Synthesis of anesthetic drug Benzocaine. (2 step synthesis)

Step-I: Synthesis of 4-aminobezoic acid from 4-nitrobenzoic acid
Chemical required: 4-nitrobenzoic acid, EtOH, H,SO4,NH,OH, pHpaper, NaCl, MgsO4,
citric acid, ethyl acetate, DCM, FoSO4.ntH,O
Apparatus required: RBF, condenser, scparating funnel, filtering flask with Buchncr funncl,
cylinder, pipette, beaker, heating mental, water bath, petri dish cte
Principle:

Reaction:

Fe&oy TH20
NHyoH
NO2

Mechanism:

C2ts H
Sn HCI
NO2 NO2 NHe

oscence, Arts, and Commerce College Khamgaon Dist. Buldana- 4444303

 _Lab-VII
Chemistry MSc-II Sem-IV_ OrganicChemistry Practical
PG Department of

Safety: before use.

1Read all chemicals label carefully when working with chemicals
goggles
2_Use rubber gloves as well as reagents such as Conc.HCVH,SOyetc
Careful use of corrosive and other
3 assembly/equipment before starting experiment
4 Check all heating/electric mixture carefully
5 Add or mix solvent to the reaction appropriate waste jar/bucket/bottle etc
6_Disposeoff so lid/liquid /solvent
waste in

Reaction condition:
Reaction Molarity
Pressure
Temperature
Reflux/Heat/M. W
End time:
Reaction Time: - - a t RT/-----C Start time:

Charge of reaction:
Charge ofreaction Eq mmol
S.N Reactants M.F M.Wt Density (g/ml)
| P-nitrobengoic qcid 1s8 9lcm S98
2. FeouS Slphate.Hydie fe Sul1so 9o 2 h2- S
3- Amnonium coxide NHyoH3S 6y 2

Procedure:

In around-bottomed flask (250 mL) with magnetic stirrer place 44,6 gof FeSO4x7H;0 in 50
mL H,0 and boil it. In the meantime, dissolve in Erlenmayer flask (250 mL) 21 g of 4
nitrobenzoic acid in 15mL 12% NH,OH (place the flask in the water bath and heat slightly to
dissolve the solid compound). Add drop wise this solution to the flask with salt FeSO4 and
stir vigorously till the forming product prevents stirring. Then shake the flask with reaction
mixture. After 20 mimutes, add slowly 15 mL of 25% NH,OH up to pH-9 (check pH for base
with pH paper). Stir additionally 20 minutes. Then the hot mixture filter on Büchner funnel.
Important is the solution!!! Acidify it with citric acid to pH-4 and move the mixture to
separatory funnel and extract (5x30 mL) with the mixture ethyl acetate/CH,Ch 1:2 (v/v).
Combine the organic layers and dry the extract over MgSO4, then filtrate through the funnel
with cotton plug to remove MgSO4. Transfer the combined fractions into a clean, dry and
weighted round-bottom flask (100 mL) and concentrate the solution on rotary evaporator.
The crude yellow erystals of 4-aminobenzo ic acid will be used to the second step of reaction.
Measure the m.p. (lit. 192 °C). Warn! The product dissolve easily in water, ethanol and ether!

Buldana-4444303
G. S. Science, Arts, and Commerce College Khamgaon Dist.
 PG Department of Chemistry MSc-I Sem-IV_Organic Chemistry
Practical Lab-VII
Step-II: Synthesis of
Chemical required: 4-amino Ethy4aminobenzoate (Benzocaine) from 4-aminobenzoic acid
citricacid, ethyl acetate, DCM,benzo acid, EtOH, HSO4, NH,OH, pH paper, NaCl MgSO..
ic
FeSO4.nH0
Apparatus required: RBF, condenser, separating funnel, filtering flask
cylinder, pipette, beaker, heating mental, magnetic stiurer with Buchner
Principle: water bath, Petri dish etc funnel.

Reaction:

Mechanism:

Buldana-4444303
G. S. Science, Arts, and Commerce CollegeKhamgaon Dist.
 OrganicChemistry Practical Lab-VI
PGDepartment of Chemistry MSc-II Sem-IV

Safety:
1 Read allchemicals label carefully before use.
with chemicals
2_Use rubber gloves as well as goggles when workingConc.HCVH,SO4etc
3_Careful use of corrosive and other reagents such as
4 Check all heating/electric assembly/equipment before starting experiment
5 Addor mix solvent to the reaction mixture carefully
6_Dispose off so lid/liquid /solvent waste in appropriate waste jar/bucket/bottle etc

Reaction condition:
Reaction Molarity
Pressure
Temperature
Reflux/Heat/M. W
Reaction Time: ---------at RT/-C Start time: End time:

Charge of reaction:
S.N Reactants M.F M.Wt Density (g/ml) Charge of reaction Eq mmol

Procedure:
In a round-bottomed flask (100 mL)
place 1 g of 4-aminobenzoic acid, 8 mL anh.
Liebig condenser and heat under reflux for 4Ethanol
and 0.6 mL of 10% oleum. Adjust the
Cool down the mixture and alkalize hours.
with aq. NH OH to pH=10. Move
separating funnel and extract with ethyl acetate (3x30 mL). the mixture to
wash this fraction with NaCl solution. Combine
Dry the extract over MgSO4, and
the organic layers and
the funnel with cotton plug to then fltrate through
and dry roundbottom flask (100 remove MgSO4. Transfer the combined fractions into a clean
mL) and concentrate the
crude product solution on rotary
on air on Petri recrystalized crystals on Buchner evaporator.
from chloroform. Filter the The
dish. Weight the product,
calculate the funnel, and dry
(lit. 92 °C). percentage yield and measure the m.p.

G. S. Science, Arts, and Commerce College

Khamgaon Dist. Buldana-4444303
 PG Department of Chemistry_MSc-I Sem-IV_Organic Chemistry Practienl Lab-VI

Result:

Name ofsynthesized M.F Molecular structure M.P % Yield Uses

compound

4-amino benzoic acid tg HI1N

88 4 0 a voluabl e
qgent /n
NHe managing pw
Ethyl-4 It telieve
aminobenzoate
(Benzocaine) pain

Conclusion: --was synthesized

and the % yield was found--LOJ
References:

College Khamgaon Dist. Buldana-4444303

G. S. Science, Arts, and Commnerce