www.ijmedres.co.in ©Copyright 2010 Medicobiological Research Publications. All rights reserved.
Int J Med Res., 2017; 1(8): 448-451
IJMBR
International Journal of
Medicobiological Research
(An International Peer Review Journal)
Journal homepage: www.ijmedres.co.in; ISSN: 0976-8971
Research Article
A Homogeneous Electrolysis Method for the Anodic Acetoxylation of Biphenyl
A. Arun Joseph Rosario and S.R. Bheeter
Department of Chemistry, St. Joseph’s College, Tiruchirappalli -620 002. Tamil Nadu, India
Corresponding author: aajrosario@gmail.com
Article information ABSTRACT
Keywords:
anodic acetoxylation,
optimization,
electrodes, supporting
electrolyte,
biphenyl.
Received on : 16.06.2017
Revised on : 20.06.2017
Accepted on : 22.06.2017
A convenient, selective and homogeneous electrolysis method was developed for the
anodic acetoxylation of biphenyl. Optimization studies were carried out on an undivided
cell equipped with platinum anode and zinc cathode using a homogeneous electrolytic
medium made up of acetonitrile solvent with a minimum amount of acetate salts as
supporting electrolyte and zinc chloride at 30-35º C. This acetoxylation was achieved
without acetic acid. The better yield (68%) was obtained when 2F of electricity was
passed. The acetoxylation was also conducted in glacial acetic acid medium. Among the
method reported so far this investigation is dealt with simple, efficient, and better way to
the acetoxylation.
1. INTRODUCTION
An optimal use of electroorganic synthesis depends
not only on the possibility to synthesis compounds
that are inaccessible by other routes or more easily
available by electrolytic methods but also to a great
extent on the availability of electrochemical cells
that can produce relatively large quantities in a short
period of time.
[1]
In industrialized production around
100 organic compounds were prepared by
electrochemical method because of its simple,
selective, cost effective, and less environmental
contamination.
[2]
The polymer bound - 4-acetoxy
biphenyl derivatives were widely used as solid
support in organic synthesis in the field of polymer.
[3]
The routine conventional method to prepare 4-
acetoxy biphenyl was expensive. Therefore the
simple electrochemical technique was followed to
prepare this compound. Moreover this
electrochemical technique was also developed
ecofriendly and economically.
[4]
In order to prepare
the 4-acetoxy biphenyl with maximum yield various
optimization studies were carried out. The
electrolysis was conducted with various cathodes
(Pt
[5]
Zn, Ni,
[6]
and graphite
[7]
), supporting
electrolytes (Et4NOAc
[8]
& Bu4NOAc
[9]
) and organic
solvents (MeCN
[10]
& MeOH
[11]
). The electrolysis
was achieved without acetic acid in the presence of
Zinc Chloride.
[12]
The electrolysis was also carried
out with various acetate salts (NaOAc,
[13]
KOAc,
[14]
and NH4OAc
[15]
) in aqueous medium.
Comparatively the organic medium gave the better
yield than the aqueous medium. This could explain
with the excellent solvent properties, better
conductivity, and ease of purification step of
acetonitrile.
2. EXPERIMENTAL
2.1. Materials and method
Biphenyl was supplied by TCI. All other reagents were of
analytical grade. The power source was used as a direct
current source for the electrolysis. An undivided glass cell