REACTION OF ACETOXYSILANES WITH HYDROXY COMPOUNDS
Table 3. Yields, physical constants, and 1H NMR spectra of alkoxy(phenoxy)acetoxysilanes
Yield,
1927
Compound
d240
n2D0
1H NMR spectrum (CDCl3), , ppm
%
93
95
Si[OC6H13]4
0.8927 1.4415 0.87 t (3H, CH3), 1.28 1.35 m (6H, CH2), 1.51 1.58 m (2H, CH2),
3.74 t (2H, OCH2)
Si[OC6H11]4
1.15 1.49 m (6H, CH2), 1.68 1.71 m (2H, CH2), 1.81 1.84 m (2H,
CH2), 3.81 3.86 m (1H, OCH)
Si[OC6H5]4
Si[OCOCH3][OC6H13]3
95
94
7.07 7.12 m (3H, Ph), 7.28 7.33 m (2H, Ph)
a
0.9323 1.4239 0.85 t (3H, CH3), 1.26 1.35 m (6H, CH2), 1.49 1.58 m (2H, CH2),
2.07 s (3H, Ac), 2.09 s (3H, Ac), 3.70, 3.72, 3.80, 3.88 t (2H, OCH2)
0.9965 1.4183 0.83 t (3H, CH3), 1.24 1.31 m (6H, CH2), 1.51 1.56 m (2H, CH2),
2.06 s (3H, Ac), 2.08 s (3H, Ac), 2.10 s (3H, Ac), 3.78, 3.87, 3.95 t
(2H, OCH2)
a
Si[OCOCH ] [OC H
]
6 13 2
95
94
94
95
93
3 2
Si[OCOCH3]3[OC6H13]a
0.78 t (3H, CH3), 1.18 1.26 m (6H, CH2), 1.46 1.52 m (2H, CH2),
2.02 s (3H, Ac), 2.04 s (3H, Ac), 2.07 s (3H, Ac), 3.73, 3.81, 3.90 t
(2H, OCH2)
a
Si[OCOCH3][OC6H11]3
1.0543 1.4641 1.11 1.46 m (6H, CH2), 1.64 1.68 m (2H, CH2), 1.78 1.82 m (2H,
CH2), 2.05 s (3H, Ac), 2.07 s (3H, Ac), 3.78 3.83, 3.89 3.96, 3.98
4.07 m (1H, OCH)
1.1043 1.4461 1.11 1.44 m (6H, CH2), 1.63 1.67 m (2H, CH2), 1.76 1.80 m (2H,
CH2), 2.03 s (3H, Ac), 2.05 s (3H, Ac), 2.07 s (3H, Ac), 3.88 3.92,
3.99 4.04, 4.11 4.15 m (1H, OCH)
a
Si[OCOCH3]2[OC6H11]2
Si[OCOCH3]3[OC6H11]a
1.12 1.45 m (6H, CH2), 1.64 1.68 m (2H, CH2), 1.79 1.82 m (2H,
CH2), 2.06 s (3H, Ac), 2.09 s (3H, Ac), 2.12 s (3H, Ac), 4.00 4.04,
4.12 4.15 m (1H, OCH)
a
Si[OCOCH3][OC6H5]3
94
93
94
1.1932 1.5398 2.18 s (3H, Ac), 2.22 s (3H, Ac), 2.24 s (3H, Ac), 7.11 7.20 m (3H,
Ph), 7.32 7.39 m (2H, Ph)
1.2109 1.5100 2.13 s (3H, Ac), 2.17 s (3H, Ac), 2.18 s (3H, Ac), 7.03 7,10 m (3H,
Ph), 7.24 7.32 m (2H, Ph)
1.2537 1.4820 2.10 s (3H, Ac), 2.14 s (3H, Ac), 2.16 s (3H, Ac), 6.99 7.08 m (3H,
Ph), 7.22 7.28 m (2H, Ph)
a
Si[OCOCH3]2[OC6H5]2
Si[OCOCH3]3[OC6H5]a
a
The given formulas correspond to the averaged product composition.
mixture was heated to 80 C, and acetic acid was dis- minarily weighed, impregnated with the prepared
tilled off overa period of 2 h under reduced pressure. solution, and kept for 1 h at room temperature. It
The mixture was cooled to room temperature and
analyzed by GLC for the corresponding alkyl (phenyl)
acetate.
was then dried in an oven for 5 h at 85 C, weighed,
and the weight loss was calculated. This procedure
was carried out at specified time intervals.
REFERENCES
Hydrolysis of acetoxyalkoxy(phenoxy)silanes in
THF. Acetoxyalkoxy(phenoxy)silane, 0.5 g, was dis-
solved in 5 ml of THF containing a required amount
of water [4 mol of H2O per mole of Si(OCOCH3)n-
(OR)4 n, where n = 0, 1, 2, 3) and 0.1 g of toluene
as internal reference. The concentration of alcohol in
the mixture was determined by GLC at specified time
intervals. The results are shown in Fig. 1.
1. Leznov, N.S., Sabun, L.A., and Andrianov, K.A.,
Zh. Obshch. Khim., 1959, vol. 29, no. 4, pp. 1276
1281.
2. Leznov, N.S., Sabun, L.A., and Andrianov, K.A.,
Zh. Obshch. Khim., 1959, vol. 29, no. 5, pp. 1518
1522.
3. Khananashvili, L.M., Khimiya i tekhnologiya elemento-
organicheskikh monomerov i polimerov (Chemistry
and Technology of Heteroelement-Containing Organic
Monomers and Polymers), Moscow: Khimiya, 1998,
pp. 323 327.
Hydrolysis of acetoxyalkoxy(phenoxy)silanes on
the surface of cellulose. A sample of acetoxyalkoxy-
(phenoxy)silane was dissolved in toluene to attain
a concentration of 40%. A paper napkin was preli-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 12 2001