ACYL IODIDES IN ORGANIC SYNTHESIS: II.
1581
2.1 s (CH3COO). Found, %: C 30.34; H4.57; I52.76.
C6H11 IO2. Calculated, %: C 29.75; H 4.54; I 52.47.
mixed with 5.8 g of phenyl ethyl ether. From the
mixture was separated by distillation 2.5 g (53%) of
ethyl iodide, bp 70 72 C, nD27 1.5022 (publ. [12]: bp
72 C, nD20 1.5137), and 2.3 g (71%) of phenyl acetate,
bp 75 C (10 mm Hg) {publ. [12]: bp 195.5 C
(760 mm Hg.)}. Found, %: C 70.1; H 5.52. C8H8O2.
Calculated, %: C 70.58; H 5.92.
Benzyl iodide reaction with 1,4-dioxane. At mix-
ing of 11 g of benzyl iodide and 2.05 g of 1,4-di-
oxane a precipitate immediately separated. The latter
was filtered off, dissolved in ethanol, reprecipitated
with water, and dried in a vacuum desiccator over
P2O5. Thus was isolated 1.43 g (23%) of 1,2-dibenzo-
yloxyethane, bp 73 C (publ. [12]: bp 73 74 C].
Found, %: C 70.66; H 5.27. C16H14O4. Calculated,
%: C 71.1; H 5.18.
REFERENCES
1. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N.,
Zh. Org. Khim., 2002, vol. 38, no. 11, pp. 1630 1632.
2. Voronkov, M.G.and Khudobin, A.Yu., Izv. Akad.
Nauk SSSR, Ser. Khim., 1956, no. 6, p. 713.
3. Voronkov, M.G. and Dubinskaya, E.I., J. Organo-
metal. Chem., 1991, vol. 410, no. 3, p. 1.
4. Olah, G.A. and Narang, S.C., Tetrahedron, 1982,
vol. 38, no. 130, p. 2225.
5. Kizhner, N., Zh. Russian Fed. Khim. Obshch.,
1909, vol. 41, no. 5, p. 651.
6. Gustus, E.L. and Stevens, Ph.G., J. Am. Chem. Soc.,
1933, vol. 55, no. 1, p. 378.
Acetyl iodide reaction with 2-ethoxyethanol. At
mixing of 10.6 g of acetyl iodide and 5.6 g of 2-eth-
oxyethanol the reaction mixture self-heated. By
distillation of the reaction mixture at the atmo-
spheric pressure we separated 4.21 g of ethyl iodide,
bp 67 72 C, nD25 1.5011 (publ. [12]: bp 72 C, nD20
1.5137), and 4.92 g (79%) of 2-hydroxy ethyl
acetate, bp 80 85 C (25 mm Hg.) {publ. [12]: bp
1
182 C (760 mm Hg.)}. IR spectrum, , cm : 3450
(OH), 2962 s, 2872 s (CH), 1750 s (C=O), 1275,
1050 s (COC). Found, %: C 46.86; H 8.31. C4H8O3.
Calculated, %: C 46.15; H 7.69.
7. Sonntag, N.O.V., Chem. Rev., 1953, vol. 52, no. 2,
p. 238.
Acetyl iodide reaction with vinyl ethyl ether.
To a solution of 5.3 g of acetyl iodide in 20 ml of
dichloromethane at 10 C was added 2.25 g of vinyl
ethyl ether. After mixing by a common distillation of
the reaction mixture was isolated 0.45 g (10%) of
vinyl iodide, bp 56 C, nD18 1.541 (publ. [12]: bp
56 56.5 C, nD20 1.5385). In the second fraction ethyl
iodide, vinyl acetate, and ethyl acetate were identified
by GLC.
8. Patai, S., The Chemistry of Acyl Halides, London,
1972, p. 177.
9. Suzuki, Y. and Matsushima, M., Chem. Lett., 1998,
no. 4, p. 319.
10. Krasusky, K.A., J. Rus. Phis. Soc., 1907, vol. 39,
p. 520.
11. Teobald, D.W. and Smith, J.C., Chem. Ind., 1958,
no. 32, p. 1007.
12. Spravochnik khimika (Chemist,s Handbook), Nikol,-
skii, B.P., Ed., Moscow: Khimiya, 1953, vol. 2,
p. 398.
Acetyl iodide reaction with phenyl ethyl ether.
At room temperature 5.31 g of acetyl iodide was
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 11 2002