ISSN 1070-3632, Russian Journal of General Chemistry, 2011, Vol. 81, No. 6, pp. 1245–1246. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © Yu.V. Popov, T.K. Korchagina, V.S. Kamaletdinova, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 6, pp. 1053–
1054.
LETTERS
TO THE EDITOR
Synthesis of 2-Methyl-2-(3-phenoxybenzoyloxy)propionitrile
Yu. V. Popov, T. K. Korchagina, and V. S. Kamaletdinova
Volgograd State Technical University, pr. Lenina 28, Volgograd, 400131 Russia
е-mail: vgdci@mail.ru
Received June 16, 2009
DOI: 10.1134/S1070363211060314
Nowadays the diphenyl oxide derivatives con-
taining versatile functional groups are of significant
practical interest. Many of them exhibit biomedical
activity, and some of them are used in the agriculture.
Of great interest in this series are nitriles, whose
molecules contain in the side chain various func-
tionalities alongside cyano group.
The synthesis was performed at room temperature
(20–25°С) under stirring for 1 h using the 3-phenoxy-
benzoic acid chloride–acetone cyanohydrine–triethyl-
amine in a molar ratio 1:1.2:1.2.
The structure and composition of the compound
1
obtained was confirmed by IR and H NMR spec-
troscopy.
We developed an effective approach towards the
synthesis of 2-methyl-2-(3-phenoxybenzoyloxy)propio-
nitrile on the basis of 3-phenoxybenzoic acid chloride
and acetone cyanohydrine which is 3-phenoxyphenyl-
containing compound of the new structure. It can be of
interest as an intermediate in the synthesis of
biologically active compounds.
2-Methyl-2-(3-phenoxybenzoyloxy)propionitrile.
To a solution of 10 g (0.0462 mol) of 3-phenoxy-
benzoic acid chloride in 30 ml of anhydrous ethyl
ether in a four-neck round-bottom flask equipped with
a mechanical stirrer, a thermometer, a dropping funnel,
and a reflux condenser bearing a calcium chloride tube
was added dropwise 5.6 g (0.05544 mol) of triethyl-
amine in 10 ml of anhydrous diethyl ether. Then to the
reaction mixture was added dropwise 4.7124 g
(0.05544 mol) of acetone cyanohydrine in 10 ml of
anhydrous diethyl ether. The synthesis was performed
under stirring at 20–25°С within 1 h. The triethyl-
amine hydrochloride precipitate was filtered off, and
the solvent was removed from the filtrate by distilling
off first at atmospheric pressure and then in a vacuum.
2-Methyl-2-(3-phenoxybenzoyloxy)propionitrile was
isolated by vacuum distillation. Yield 12.3 g (95%), a
very viscous liquid of dark color, bp 190–192°С (3
The incorporation of 3-phenoxyphenyl fragment in
the pharmacophore molecule is a promising way to the
synthesis of the new biologically active substances
[1–4].
2-Methyl-2-(3-phenoxybenzoyloxy)propionitrile was
obtained by the reaction of the 3-phenoxybenzoic acid
chloride with acetone cyanohydrine in the anhydrous
diethyl ether in the presence of triethylamine as the
hydrogen chloride acceptor:
O
1
CH3
mm Hg). H NMR spectrum, δ, ppm: 1.8 s (6Н, СН3),
O
C
6.9–7.8 m (9Н, С6Н5ОС6Н4). IR spectrum, ν, cm–1: 2224
(CN), 2938 (СН), 1287 (5СН3), 1732 (С=О).
Cl
+
HO
O
C
CN
CH3
The IR spectrum was recorded on a Specord M-82
spectrophotometer (mull in mineral oil, NaCl or KBr
O
C
CH3
1
C
C
prisms). The Н NMR spectrum was registered on a
O
N
(C2H5)3N
_HCl
Varian Mercury 300BB spectrometer (DMSO-d6),
CH3
internal reference HMDS.
1245
Popov, Yu. V.
