Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 5, pp. 929−931.
Pleiades Publishing, Ltd., 2010.
Original Russian Text
L.B. Beresnevich, K.L. Moiseichuk, N.A. Zhukovskaya, E.A. Dikusar, 2010, published in Zhurnal Prikladnoi Khimii, 2010, Vol. 83,
No. 5, pp. 876−877.
Preparative Synthesis of 1,2-Propyleneglycolacetals
L. B. Beresnevich, K. L. Moiseichuk, N. A. Zhukovskaya, and E. A. Dikusar
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belasrus
Received July 15, 2009
Abstract—The article describes a preparative method for the synthesis of new 1,2-propyleneglycolacetals
of 3-alkoxy-4-acyloxy-benzaldehydes obtained by condensation of 3-alkoxy-4-acyloxybenzaldehydes with
1,2-propylene glycol in the medium of boiling benzene in the presence of the FIBAN K-1 sulfonic cation-
1,2-Propyleneglycolacetals or 1,3-dioxolanes, which
are derivatives of aldehydes used as components of odor-
ous materials and odorants, are more stable than initial
aldehydes, especially in relation to an alkaline medium.
This circumstance stimulates studies in the ﬁ eld of the
synthesis of new cyclic acetals, which keep the main spec-
trum of odor and allow its nuances to be obtained. Ethyl-
ene glycol [1–4], glycerin [2, 5], 1,2-cyclohexanediol ,
2,3- butylenes glycol [1,7], and 1,2-propylene glycol are
used as vicinal glycols for obtaining 1,3-dioxolanes .
It was reported earlier about the synthesis of 1,2-pro-
pyleneglycolacetals of some natural aldehydes and
ketones with the use of the FIBAN K-1 sulfonic cation-
exchange resin as a catalyst . Advantages of its use in
comparison with such traditional catalysts as pyridine
hydrochlorides, triethylamine, or carbamide , and
KRS-40 cation-exchange resin have been shown.
The present work describes the preparative method
of the synthesis of new 1,2-propyleneglycolacetals
of 3-alkoxy-4-acyloxybenzaldehydes (IIIa–IIIf) and
(IVa–IVf) obtained by condensation of 3-alkoxy-4-
acyloxybenzaldehydes (I) with 1,2-propylene glycol
(II) in the medium of boiling benzene in the presence of
FIBAN K-1 sulfonic cation-exchange resin as a catalyst
and following distillation of water formed during the
reaction using a Dean–Stark’s trap. The duration of the
synthesis is 12–14 h, and the yield of target compounds
is 80–97% (see the scheme).
The developed procedure of the synthesis makes it
possible to produce experimental-industrial amounts of
acetals IIIa–IIIf, IVa–IVf and of some other carbonyl
compounds and to obtain them with purity sufﬁ cient
for application as food ﬂ avors . The application of
FIBAN K-1 sulfonic cation-exchange resin prevents the
alcoholysis of labile ester groups and simpliﬁ es separat-
ing of main products.
Synthesized compounds IIIa–IIIf and IVa–IVf rep-
resent colorless or weakly colored liquids, they do not
require additional reﬁ ning and do not contain admixtures
of mother compounds. The structure of acetals IIIa–IIIf
R – CH
СН (d), СН