VINYLATION OF HYDROXY-CONTAINING CYCLIC FORMALDEHYDE ACETALS
1437
1
Delfort, B., Hillion, G., and Durand, I., FR Patent
no. 2866654, 2004; Chem. Abstr., 2006, vol. 143,
no. 250957.
CH=, CH2=, ring). H NMR spectrum, δ, ppm: com-
pound V: 6.34 d.d (1H, =CHO), 4.30 d.d (1H, =CHtrans
,
3J = 14.4, J = 1.8 Hz), 4.09 d.d (1H, =CHcis, J = 6.6,
2
3
2J = 1.8 Hz), 4.84 d and 4.76 d (1H each, 2-H, J =
2
8. Rodier, J.-D. and Mahler, B., PCT WO 2005/105149,
6.1 Hz), 4.03 m and 3.73 d.d (4H, 4-H, 6-H, 2J = 11.8,
3J = 5.6 Hz), 3.89 m (5-H); compound VI: 6.45 d.d
2005; Chem. Abstr., 2006, vol. 143, no. 410646.
9. Bell, A.R., Shephard, R.W., Iemma, S., and Stajic, V.,
PCT WO 2007/062483, 2007; Chem. Abstr., 2007,
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tsiklicheskikh atsetalei (New Trends in the Chemistry of
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1957, vol. 27, p. 2840; Mikhant’ev, B.I. and Lapen-
ko, V.L., Zh. Obshch. Khim., 1957, vol. 27, p. 2972;
Mikhant’ev, B.I. and Lapenko, V.L., Zh. Obshch. Khim.,
1961, vol. 31, p. 1843; Mikhant’ev, B.I., Lapenko, V.L.,
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Grzeszczyk, B., Matyjasek, L., and Chmielewski, M.,
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erski, A., Solecka, J., Urbanczyk-Lipkowska, Z., and
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3
2
(1H, =CHO), 4.18 d.d (1H, =CHtrans, J = 14.3, J =
3
2
1.8 Hz), 4.00 d.d (1H, =CHcis, J = 6.8, J = 1.8 Hz),
5.02 s and 4.88 s (1H each, 2-H), 4.25 m (1H, 4-H),
3.95 m (2H, 5-H), 3.69 m (2H, OCH2). 13C NMR spec-
trum, δC, ppm: compound V: 149.47 (CH=), 93.21 (C2),
88.87 (CH2=), 68.20 (C4, C6), 65.91 (C5); compound
VI: 151.41 (CH=), 95.00 (C2), 86.78 (CH2=), 73.20
(C4), 68.41 (C5), 65.91 (CH2). Found, %: C 55.38;
H 7.87. C6H10O3. Calculated, %: C 55.37; H 7.74.
Vinylation of 2-methoxyethanol. A 1-l steel rotat-
ing high-pressure reactor was charged with 22.4 g
(0.29 mol) of 2-methoxyethanol and 2.2 g (10 wt %)
of potassium hydroxide, acetylene was supplied to
a pressure of 12 atm, and the mixture was heated for
2 h at 115–120°C. Distillation (105–115°C) gave
22.8 g of a substance containing 22% of unreacted
2-methoxyethanol (GLC). Yield of 1-methoxy-2-vinyl-
oxyethane 17.8 g (60%).
This study was performed under financial support
by the President of the Russian Federation (program
for support of leading scientific schools, project
no. NSh-263.2008.3).
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 10 2008