Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 10, pp. 1871−1876.
Pleiades Publishing, Ltd., 2009.
Original Russian Text A.M. Magerramov, M.R. Bairamov, I.A. Aliev, M.A. Agaeva, M.G. Allakhverdieva, I.G. Mamedov, M.A. Dzhavadov, 2009, published in
Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 10, pp. 1719−1724.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of 1-(4-Isopropenylphenoxy)-bromo-С
and Application of Their Transformation Products
A. M. Magerramov, M. R. Bairamov, I. A. Aliev, M. A. Agaeva, M. G. Allakhverdieva,
I. G. Mamedov, and M. A. Dzhavadov
Baku State University, Baku, Republic of Azerbaijan
Received December 3, 2008
Abstract—Reaction of 4-isopropenylphenol with α,ω-dibromo-С
-alkanes by the Willamson reaction in the
presence of potassium iodide as promoter, aiming to synthesize the corresponding monobromosubstituted derivatives
and to study their some chemical transformation. Optimal conditions to obtain 1-(4-isopropenylphenoxy)-2-
bromoethane, 1-(4-isopropenylphenoxy)-3-bromopropane and 1-(4-isopropenylphenoxy)-4-bromobutane were
found. The nitrogen-containing derivatives, inhibitors of a hydrosulfuric corrosion in the water-salt solutions, were
obtained on the basis of the first two compounds. The derivatives involving multiple bond and ester-group were
synthesized from the third compound. Their incorporation into the polystyrene chains in the process synthesis
gives them plasticize properties.
Alkenylphenols and their derivatives are of quiet
various uses [1–6]. Their reactions with halogen-
containing alkanes by Willamson, in particular with
symmetric dihalogenalkanes, promise interesting
resultes. They enable synthesis of new phenol derivatives
containing multiple bond С=С and halogen atom, and as
a result they can be used as intermediate for the further
It was shown in the work  that di(4-isopropenyl-
phenoxy)alkanes are dominantly formed by the reaction
of 4-isopropenylphenol (4-IP) with α,ω-dihalogen-
-alkanes in the presence of potassium hydroxide.
However, the further investigations showed that, among
them, (4-isopropenylphenoxy)halogens were formed
too. A study of an inﬂ uence of such various factors
as a temperature and ratio of reagents on the reaction
progress has shown that the molar ratio of the used
substances effects essentially on a composition of end
In this work we present results of studying the reactions
of 1,2-dibromoethane (DBE), 1,3-dibromopropane (DBP)
and 1,4-dibromobutane (DBB) with 4-IP for the purpose
of synthesis of the corresponding bromoalkyl derivatives,
and of studying their some transformations.
The reactions of DBE, DBP and DBB with 4-IP were
carried out by Scheme 1.
Results of performed investigation show, that the
temperature and molar ratio of reagents in the mixture effect
signiﬁ cantly on formation of the monobromosubstituted
derivatives DBE, DBP and DBB.
Experiments for search of optimal conditions
providing a good yield were conducted by the example
of DBB and 4-IP at the different temperatures and
molar ratio of DBB and 4-IP 1:1. We have found that as
temperature is increased from 20 to 80°С the yield of
monobromine-containing compound grows from 3.4 to
47.8%. Further temperature increase to 100°С leads to
decrease in its yield to 45.1%. The side reaction of 4-IP
dimerization enhances under these conditions.
An obtained dependence of 1-(4-isopropenylphenoxy)-
4-bromobutane yield on the molar ratio DBB : 4-IP at
the found optimal temperature 80°С are given on the
The maximum yield, 64.2%, compound III was
obtained at the molar ratio of DBB and 4-IP 1.5 : 1.
Further increase of DBB amount in the initial mixture