Conditions for the Reaction of Furfural with Glycerol. In a three-neck flask fitted with a stirrer, a
reflux condenser, and a Dean–Stark tube we placed furfural (19.2 g, 200 mmol), glycerol (18.4 g, 200 mmol),
benzene (80 ml), and p-toluenesulfonic acid (0.011 g). The mixture was boiled for 3 h with stirring. The end of
the reaction was determined by the cessation of the deposition of water in the trap. After distillation of the
solvent the product was isolated by vacuum distillation. We obtained 25.5 g (75%) of the condensation product.
Found %: C 56.8; H 5.40. C H O . Calculated %: C 56.5; H 5.90.
8
10
4
Distribution of the Isomers of 2-Furyl-1,3-dioxacyclanes. The mixture of isomers weighing 1.2 g was
separated on a column (3.5 × 18 cm) of silica gel L 40/100 with mixtures of hexane and ether in ratios of 7:3
(
450 ml) and 1:1 (350 ml) or ether (300 ml) as eluant. With the first mixture of solvents we eluted 0.05 g of the
oily compound 2, which gradually crystallized. With the second mixture we eluted 0.75 g of a liquid fraction
containing the acetals 3 and 4. With ether we eluted the crystalline compound 1. The separation of the isomers
was monitored by TLC on Silufol UV-254 plates with a 1:1 mixture of hexane and ether as eluant. A 2N solution
of 2,4-dinitrophenylhydrazine was used as developer.
1
3
cis-Hydroxy-2-(2-furyl)-1,3-dioxane (1). C NMR spectrum, δ, ppm: 63.2, 67.7, 77.5, 98.5 (С(5),
С(4), С(6), С(2) (1,3-dioxacycle), 109.6, 113.4, 143.9, 152.0 (С(3), С(4), С(2), С(5) (furan ring).
REFERENCES
1.
2.
3.
V. G. Kalashnikova, V. G. Kul'nevich, Z. I. Zelikman, and E. V. Gromachevskaya, KPI, Dep. VINITI,
Krasnodar, No. 8, 70 (1979).
Z. I. Zelikman, V. G. Kul'nevich, and V. G. Kalashnikova, USSR Inventor's Certificate 694168, Byull.
Izobr., No. 40, 18 (1979).
N. I. Nen'ko, T. P. Kosulina, V. G. Kul'nevich, V. P. Smolyakov, G. E. Gonik, Yu. S. Pospelova,
L. L. Knor, A. Ya. Barchukova, E. P. Aleshin, and P. A. Galenko-Yaroshevskii, Russian Federation Pat.
2
042326; Byull. Izobr., No. 24, 100 (1995).
4
5
.
.
V. G. Kul'nevich, L. A. Badovskaya, and V. M. Latashko, Regulators of the Development and Growth of
Plants. Conference Abstracts [in Russian], Moscow (1991), p. 55.
V. G. Kul'nevich, Z. I. Zelikman, V. G. Kalashnikova, E. V. Gromachevskaya, E. F. Lavretskaya, and
L. T. Chamorovskaya, USSR Inventor's Certificate 759519; Byull. Izobr., No. 32, 103 (1980).
Z. I. Zelikman, Izv. Vuzov. Pishchevaya Tekhnologiya, 10, No. 5, 116 (1967).
6
7
.
.
V. G. Kul'nevich and Z. I. Zelikman, USSR Inventor's Certificate 253044; Byull. Izobr., No. 5, 17
(
1969).
8
9
.
.
Z. I. Zelikman and V. G. Kul'nevich, Izv. Vuzov. Pishchevaya Tekhnologiya, 12, 916 (1969).
Z. I. Zelikman, L. A. Falina, A. I. Shkrebets, and B. G. Kul'nevich, Izv. Vuzov. Pishchevaya
Tekhnologiya, 16, 1382 (1973).
1
1
1
0.
1.
2.
V. G. Kul'nevich and Z. I. Zelikman, Khim. Geterotsikl. Soedin., 367 (1969).
V. G. Kul'nevich and Z. I. Zelikman, Zh. Org. Khim., 7, 573 (1971).
A. I. Shkrebets, Z. I. Zelikman, V. G. Kul'nevich, and R. Z. Fakhrutdinov, Khim. Geterotsikl. Soedin.,
1
159 (1972).
1
1
3.
4.
Z. I. Zelikman, A. I. Shkrebets, and V. G. Kul'nevich, Kinet. Katal., 16, 1128 (1975).
F. V. Nevolin, Chemistry and Technology of Glycerol Production [in Russian], Nauka, Moscow (1965),
p. 256.
1
1
5.
6.
A. I. S. Blaga, S. Ferenezi, R. F. Pape, M. A. Vincze, R. V. Vladea, and T. V. Chirila, Rom. Pat. 63233;
Chem. Abstr., 92, 24389 (1980).
H. Zaschke, H. M. Vorbrodt, D. Demus, and W. Weissflog, DDR Pat. 139852; Chem. Abstr., 93, 213415
(
1980).
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