HYDROLYSIS OF 2-[2-(VINYLOXY)ETHOXYMETHYL]OXIRANE
27%, bp 163–165°C (1 mm), d420 = 1.2084, nD20
1113
=
REFERENCES
1.4730; published data [4]: bp 153–157°C (1 mm),
d240 = 1.1690, nD20 = 1.4720; MRD = 31.61, calcd. 31.52.
Found, %: C 43.98; H 8.97. C5H12O4. Calculated, %:
C 44.11; H 8.88.
1. Trofimov, B.A., Geteroatomnye proizvodnye atsetilena
(Heteroatom Acetylene Derivatives), Moscow: Nauka,
1981, p. 38; Trofimov, B.A., Irkutskii institut khimii imeni
A.E. Favorskogo (Favorskii Irkutsk Institute of Chem-
istry), Trofimov, B.A., Ed., Novosibirsk: Sib. Otd. Ross.
Akad. Nauk, 2001, p. 100.
2. Shostakovskii, M.F., Atavin, A.S., Vyalykh, E.P., Trofi-
mov, B.A., and Tatarinova, A.F., Zh. Org. Khim., 1967,
vol. 3, p. 1972.
3. Trofimov, B.A., Deriglazov, N.M., Minakova, T.T., Brod-
skaya, E.I., Tandura, T.A., and Kul’gavova, T.V., Izv.
Akad. Nauk SSSR, Ser. Khim., 1980, p. 2707.
4. Trofimov, B.A., Minakova, T.T., Tandura, T.A., Brod-
skaya, E.I., and Deriglazov, N.M., Izv. Sib. Otd. Akad.
Nauk SSSR, Ser. Khim. Nauk, 1982, issue 3, p. 2707.
5. Malinovskii, M.S., Okisi olefinov i ikh proizvodnye
(Olefin Oxides and Their Derivatives), Moscow: Gos-
KhimIzdat, 1961, p. 174; Elderfield, R.C. and Short, F.,
Heterocyclic Compounds, Elderfield, R.C., Ed., New
York: Wiley, 1956, vol. 5. Translated under the title
Geterotsiklicheskie soedineniya, Moscow: Inostrannaya
Literatura, 1961, vol. 5, p. 7.
6. Reese, C.B., Protective Groups in Organic Chemistry,
McOmie, J.F.W., Ed., London: Plenum, 1973. Translated
under the title Zashchitnye gruppy v organicheskoi
khimii, Moscow: Mir, 1976, p. 97.
2-(2-Methyl-1,3-dioxolan-4-ylmethoxy)ethanol
(IV) was isolated from the ether extract by distillation.
Yield 30%, bp 88–90°C (2 mm), d420 = 1.0932, nD20
=
1.4455; published data [7]: bp 113–115°C (8 mm),
nD20 = 1.4453. IR spectrum, ν, cm–1: 3400, 2990, 2920,
2865, 1470, 1450, 1400, 1360, 1330, 1305, 1260, 1205,
1130, 1105, 1050, 1010, 920, 860, 715, 690, 610, 520.
1H NMR spectrum, δ, ppm: 1.35 d (1.4H, Me, cis, 3J =
3
4.8 Hz), 1.38 d (1.6H, Me, trans, J = 4.8 Hz),
2.90 br.s (1H, OH), 3.6–4.3 m (9H, OCH2, 4-H), 5.01 q
(1.1H, 2-H, trans, 3J = 4.8 Hz), 5.11 q (0.9H, 2-H, cis,
3J = 4.8 Hz). 13C NMR spectrum, δC, ppm: trans iso-
mer: 19.74 (CH3), 61.57 (CH2OH), 67.14 (C5), 72.16
(4-CH2), 72.89 (CH2CH2OH), 75.05 (C4), 102.07 (C2);
cis isomer: 19.79 (CH3), 61.57 (CH2OH), 67.24 (C5),
71.64 (4-CH2), 72.89 (CH2CH2OH), 74.66 (C4), 101.48
(C2). Found, %: C 51.96; H 8.73. C7H14O4. Calculated,
%: C 51.84; H 8.70.
The IR spectra were recorded on a Specord 75IR
1
spectrometer from thin films. The H and 13C NMR
spectra were measured on a Bruker DPX-400 instru-
ment at 400 and 100 MHz, respectively, using CDCl3
as solvent and HMDS as internal reference.
7. Kharasch, M.S. and Nudtnberg, W., J. Org. Chem., 1943,
vol. 8, p. 189; Kharasch, M.S., US Patent no. 2428805,
1947; Chem. Abstr., 1948, vol. 42, p. 618.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 7 2009