SYNTHESIS OF 4-METHOXY-N-ANILINE

SARAH THATO MODUKANELE

14001889
FORENSIC SCIENCE
CHEM405
INTRODUCTION

Green chemistry is the design of chemical products and processes that reduce or eliminate the
use or generation of hazardous substances. Green chemistry applies across the life cycle of a
chemical product, including its design, manufacture, use, and ultimate disposal. Green
chemistry is also known as sustainable chemistry (J Hunt, 2000). One of the reasons for its use
is to reduce the negative impacts of chemical products and processes on human health and the
environment, reduce the formation of waste products and it results in source reduction because
it prevents the generation of pollution (Bruice P, 2013). There are other methods to perform
this experiment but this was a preferred method for the above mentioned reasons.

Schiff base was invented by Hugo Schiff, which is named after him (J Hunt, 2000). Schiff
bases are an important class of ligands in coordination chemistry and find extensive application
in different fields. Schiff bases derived from aromatic carbonyl compounds. The first step of
the mechanism during the Schiff Base formation is the nucleophilic attack of an amine on the
electrophilic carbonyl carbon of aldehyde to form an imine and is a reversible step. The
formation of a Schiff base from an imine largely depends on the rate of removal of water which
in the green chemistry is done by roughly grinding the reagents together to avoid accumulation
of water.
EXPERIMENTAL PROCEDURE

The reaction mixture of aniline (10mmol) and 4-hydroxybenzaldehyde (1.22g) was ground
thoroughly using a pestle and mortar for about 15minutes. The crude product was then purified
by crystallization from ethanol and the pure Schiff base was obtained. TLC was then ran to
monitor the progress of the reaction. Plates had three spots (or lanes) on the origin: one for the
main organic starting material that is being transformed, one for a co-spot (starting material
and the reaction mixture), and one for the reaction mixture.

RESULTS

Rf = 0.71
DISCUSSION

The reaction equation is:

OH + H2N O NH2

4-hydroxybenzaldehyde aniline 4-Methoxyaniline

The reaction between a carbonyl compound and an amine leading to the formation of Schiff
bases is a facile reaction due to the good electrophilic and nucleophilic characteristic properties
of the carbonyl and amine groups, respectively. In this experiment, the 4-Methoxyaniline was
formed successfully and the results of the TLC show a significant variation between the product
and the reaction mixture. After recrystallization the yellow crystals that were formed were
mixed with a yellow and white powder formed during recrystallization. It is possible that this
powder was some of the unreacted material that was left during the recrystallization process.

Conclusion

The green chemistry method is a new eco-friendly grinding method for the synthesis of Schiff
bases with a good calculated percentage yield of 86%. The products can be purified by
recrystallization using ethanol. Compared with traditional methods, this solvent-free approach
is more convenient, cleaner, and safe, does not employ any toxic materials, and involves mild
reaction conditions and simple workup which results in maximum efficiency.

References
Bruice, P. (2013). Organic Chemistry, 7th ed. New Jersey: Pearson.

field, c. j. (2012). Advanced organic chemistry. New Delhi: Springer.

J Hunt, A. R. (2000). chemistry. New York: McGraw Hills.

Striegel, M., & Hill, J. (1996). Thin-layer Chromatography for Binding Media Analysis. United
States of America: The J. Paul Getty Trust.

T.W. Graham Solomon’s, C. B. (2011). Organic Chemistry. John Wiley and Sons.