Synthesis of 3-phenoxyphenylmethoxypropionitrile

Full text of DOI:10.1134/S1070363210060344

ISSN 1070-3632, Russian Journal of General Chemistry, 2010, Vol. 80, No. 6, p. 1219. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © Yu.V. Popov, T.K. Korchagina, V.S. Kamaletdinova, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 6, pp. 1051–
1
052.
LETTERS
TO THE EDITOR
Synthesis of 3-Phenoxyphenylmethoxypropionitrile
Yu. V. Popov, T. K. Korchagina, and V. S. Kamaletdinova
Volgograd State Technical University, pr. Lenina 28, Volgograd, 400131 Russia
е-mail: viktori_2008@bk.ru
Received December 9, 2009
DOI: 10.1134/S1070363210060344
Nitriles of the series of diphenyl oxide functional
There is a special interest in the synthesis of
molecules, which besides diphenyloxide fragment and
nitrile group contain in the side chain functional
groups, since combination of different pharmacophores
in the structure must lead to expansion of biological
activity range of the target compounds [1–4].
derivatives, whose molecules contain in the side chain
different functionalities along with nitrile group, are of
great interest. These compounds exhibit the biological
activity of various types and also they can be used as
starting materials for the synthesis of some derivatives
possessing medical-biological properties.
New effective synthetic approach to 3-phenoxy-
phenylmethoxypropionitrile, starting from 3-phenoxy-
benzyl alcohol and acrylonitrile, was developed. This
compound is a 3-phenoxyphenyl-containing product
new by structure and can be of interest as semiproduct
in the synthesis of biologically active compounds.
The 3-phenoxyphenylmethoxypropionitrile was ob-
tained by the reaction of 3-phenoxybenzyl alcohol with
acrylonitrile in anhydrous benzene in the presence of
4
0% solution of potassium hydroxide along the
following scheme:
O
CH2 OH
O
CH2
O
CH2 CH2
C
N
KOH
+
CH2 CH C
N
The synthesis was performed at reagents molar
ratio 3-phenoxybenzyl alcohol:acrylonitrile 1:1.2–1.5
at the boiling point of benzene, 80–82°C.
ppm: 6.659–7.102 m (9Н, С
Ar–CH
t (2Н, –СH
6
Н
5
ОС
6
Н
4
); 4.245 s (2Н,
–); 2.232–2.275
2
–); 3.320–3.362 t (2Н, О–СH
–CN).
2
2
The obtained nitrile was isolated by the vacuum
distillation [bp 182–185°С (3 mm Hg)] as colorless
liquid in 85% yield.
IR spectrum was recorded on a SPEKORD M-82
and PERKIN-ELMER instruments (film). Н NMR spec-
trum was registered on a Varian Mercury 300BB instru-
ment relative to internal HMDS in carbon tetrachloride.
1
The structure and the composition of nitrile obtained
1
was confirmed with IR and H NMR spectroscopy.
REFERENCES
3
-Phenoxyphenylmethoxypropionitrile. A mix-
ture of 10 g (0.05 mol) of 3-phenoxybenzyl alcohol,
.2 g (0.075 mol) of acrylonitrile, 20 ml of anhydrous
1
.
Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya,
primeneniye (Pesticides. Chemistry,Ttechnology, Appli-
cation), Moscow: Khimiya, 1987.
4
benzene, and 1.5 ml of 40% potassium hydroxide
solution was stirred for 5 h at 80–82°С. Then the
reaction mixture was filtered; the benzene layer was
separated, washed with distilled water to neutral pH,
concentrated, and distilled. Yield 10.7 g (0.042 mol,
2
3
.
.
Chicherina, G.V., Cand. Sci. (Chem.) Dissertation,
Volgograd, 1998.
Ermakova, T.A., Cand. Sci. (Chem.) Dissertation,
Volgograd, 2002.
4. Khimicheskaya Entsyklopediya (Chemical Encyclopedia),
Knunyants, I.L., Ed., Moscow: Bol’shaya Rossiiskaya
Entsyclopediya, vol. 3, 1992, p. 1042.
–
1
8
5%), bp 182–185°С (3 mm Hg). IR spectrum, ν, cm :
1
2
218 (С≡N); 980 (С–О–С). Н NMR spectrum, δ,
1
219