Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 4, pp. 525−528.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © M.K. Mamedov, E.G. Makhmudova, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 4, pp. 563−566.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of Diesters by Addition of Saturated Carboxylic
Acids to Tricyclodecenyl Formate
M. K. Mamedov and E. G. Makhmudova
Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received December 18, 2012
Abstract—Reaction of addition of C
-saturated monobasic acids to tricyclo[126.96.36.199
mate in the presence of a catalyst, boron triﬂ uoride etherate (BF
), was used to synthesize homo- and mixed
]decane-3(4),8(9)-diol diesters. The synthesized formic-acetic and formic-propionic acid diesters
have a pleasant odor and can be used as components for preparation of perfume formulations.
It is known that tricyclo[188.8.131.52
(TCDOL) monoesters can be synthesized via addition of
saturated monobasic acids (SMAs) to tricyclo[184.108.40.206
deca-3,8-diene (TCD) in the presence of catalysts, inor-
ganic acids H
[1–3], or thermally [4, 5].
It has been shown that synthetic tricyclic TCDOL mono-
esters are plasticizers for polymeric materials  and
fragrance compounds for fabrication of perfume formula-
tions: colognes and perfumes .
To expand the assortment of fragrance compounds,
we studied the reactions of SMA addition to tricy-
]dec-3-en-8(9)-yl formate (I) synthesized
by the method described in , with BF
catalyst. The reaction occurs by the scheme
R = H (II), CH
CH (VI), CH
To ﬁ nd the optimal conditions for the reaction of
diester formation, we examined the inﬂ uence exerted by
various factors: temperature varied within the range 40–
120°C; (I) : [(II)–(VII)] molar ratio [varied within the
range 1 : (1–2.5) for the example of formic acid (II)];
amount of BF
catalyst, 0.2–1.0% relative to the
SMA mass; and run duration, 1–5 h.
The effect of temperature and I : II molar ratio on
the yield of the diester is illustrated by the ﬁ gure. It can
Effect of (1) temperature T and (2) (I) : (II) molar ratio on the
yield Y of TCDDOL diformate.
I : II