9
1
52
KHUSNUTDINOV et al.
2
1
5
12
3.58 (CH ), 17.76 (C ), 35.83 (C ), 69.39 (C ), 76.85
C ). Found, %: C 72.81; H 13.05. C H O . Calculat-
3
14 30
2
4
(
C ), 155.11 (C=O). Found, %: C 55.23; H 7.68.
ed, %: C 72.99; H 13.12.
C H O . Calculated, %: C 55.37; H 7.74.
6
10
3
Dodecane-1,12-diyl dimethyl biscarbonate (Xc).
1
3
2
,5-Dimethoxyhexane (VIIb). Yield 98%,
Yield 80%, bp 167–168°C (1 mm). C NMR spec-
3 10 2 11
1
3
bp 78.5–79°C (80 mm). C NMR spectrum, δ , ppm:
trum, δ , ppm: 25.47 (C , C ), 28.43 (C , C ), 29.05
C
C
1
6
3
4
4 6 7 9 5 8
2
3.31 (C , C ), 31.60 (C , C ), 56.98 (OCH ), 75.57
(C , C , C , C ), 29.52 (C , C ), 54.34 (OCH ), 67.75
3
3
2
5
1 12
(
C , C ). Found, %: C 65.64; H 12.37. C H O . Cal-
(C , C ), 155.59 (C=O). Found, %: C 60.18; H 9.42.
C H O . Calculated, %: C 60.35; H 9.50.
8
18
2
culated, %: C 65.71; H 12.41.
1
6
30
6
Methyl 5-methoxypent-2-yl carbonate (VIIc).
1
3
REFERENCES
Yield 50%, bp 77.2–78°C (4 mm). C NMR spectrum,
C
(
(
1
4
3
δ , ppm: 23.14 (C ), 31.23 (C ), 35.93 (C ), 54.43
2
5
1. Aricò, F. and Tundo, P., Russ. Chem. Rev., 2010,
OCH ), 56.73 (OCH ), 67.43 (C ), 75.29 (C ), 155.44
3
3
vol. 79, no. 6, p. 479.
C=O). Found, %: C 56.69; H 9.48. C H O . Calcu-
9
18
4
2
3
4
5
. Pacheco, M.A. and Marshall, C.L., Energy Fuels, 1997,
lated, %: C 56.82; H 9.54.
vol. 11, p. 2.
Hexane-2,5-diyl dimethyl biscarbonate (VIId).
. Shaikh, A.-A.G. and Sivaram, S., Chem. Rev., 1996,
1
3
Yield 50%, bp 94–95°C (1 mm). C NMR spectrum,
vol. 96, p. 951.
1
6
3
4
δ , ppm: 23.55 (C , C ), 34.78 (C , C ), 54.43 (OCH ),
C
6
3
. Tundo, P., Memoli, S., Herault, D., and Hill, K., Green
Chem., 2004, vol. 6, p. 609.
. Keller, T., Holtbruegge, J., Niesbach, A., and Gorak, A.,
Ind. Eng. Chem. Res., 2011, vol. 50, p. 11073.
6. Gooden, P.N., Bourne, R.A., Parrott, A.J., Bevina-
katti, H.S., Irvine, D.J., and Poliakoff, M., Org. Process
Res. Dev., 2010, vol. 14, p. 411.
2
5
8.02 (C , C ), 155.76 (C=O). Found, %: C 51.05;
H 7.69. C H O . Calculated, %: C 51.27; H 7.75.
10
18
6
1
,6-Dimethoxyhexane (VIIIb). Yield 97%, bp 74–
1
3
7
(
4.5°C (30 mm). C NMR spectrum, δ , ppm: 28.23
C
3 4 2 5 1 6
C , C ), 32.29 (C , C ), 61.60 (OCH ), 72.43 (C , C ).
3
Found, %: C 65.65; H 12.38. C H O . Calculated, %:
8
18
2
C 65.71; H 12.41.
Hexane-1,6-diyl dimethyl biscarbonate (VIIIc).
7. Khusnutdinov, R.I., Shchadneva, N.A., and Mayako-
va, Yu.Yu., Russ. J. Org. Chem., 2014, vol. 50, p. 790.
1
3
8
9
. North, M., Pasquale, R., and Young, C., Green Chem.,
2010, vol. 12, p. 1514.
Yield 98%, bp 102–103°C (1 mm). C NMR spec-
3
4
2
5
trum, δ , ppm: 25.23 (C , C ), 32.14 (C , C ), 54.34
C
1
6
. Sakakura, T., Choi, J.-C., and Yasuda, H., Chem. Rev.,
(
OCH ), 67.86 (C , C ), 155.98 (C=O). Found, %:
3
2
007, vol. 107, p. 2365.
C 51.08; H 7.67. C H O . Calculated, %: C 51.27;
1
0
18
6
1
0. Fluka. Khimicheskie reaktivy dlya laboratornykh i
analiticheskikh rabot. Rossiya (Fluka. Laboratory and
Analytical Chemicals. Russia), 2009–2010.
H 7.75.
,5-Dimethoxy-3-oxapentane (IXb). Yield 95%,
bp 80–80.5°C (60 mm) {bp 162°C [11]}.
,12-Dimethoxydodecane (Xb). Yield 95%,
1
1
1. Aldrich. Katalog spravochnik khimicheskikh reaktivov
1
(Aldrich Catalog Handbook of Chemicals), 2012–2014.
1
3
bp 102–103°C (2 mm). C NMR spectrum, δ , ppm:
C
12. Dictionary of Organic Compounds, Buckingham, J.,
Ed., New York: Chapman and Hall, 1982, 5th ed.,
vols. 1–5.
3
10
6
7
5
8
2
(
6.05 (C , C ), 29.65 (C , C ), 29.90 (C , C ), 30.05
4 9 2 11 1
C , C ), 30.24 (C , C ), 58.40 (OCH ), 72.85 (C ,
3
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 7 2014