Molecules 2002, 7
392
Carbonic acid benzyl ester hexyl ester (n-C6H13OCO2CH2Ph). A colorless liquid; 300 mg, 67%; IR
1
(CHCl3) ν 1744 cm-1 (C=O); H-NMR: δ 0.88-0.90 (3H, m, CH3), 1.31-1.41 (6H, m, CH2), 1.61-1.71
(2H, m, CH2), 4.10- (2H, t, J = 6.9 Hz, CH2), 5.16 (2H, s, CH2), 7.33-7.41 (5H, m, Ar); MS (EI) m/z
236 (M+); [Calc. for C14H20O3: requires M, 236.1412. Found: 236.1372 (M+)].
Carbonic acid benzyl ester 3-phenylpropyl ester [Ph(CH2)3OCO2CH2Ph]. A colorless liquid; 291 mg,
1
69%; IR (CHCl3) ν 1723 cm-1 (C=O); H-NMR: δ 1.98-2.07 (2H, m, CH2), 2.71-2.78 (2H, m, CH2),
4.17-4.23 (2H, m, CH2), 5.19 (2H, s, CH2), 7.21-7.40 (5H, m, Ar); MS (EI) m/z 208 (M+-60); [Calc. for
C17H18O3: requires M, 270.1256. Found: 270.1245 (M+)].
Carbonic acid benzyl ester heptyl ester (n-C7H15OCO2C4H9). A colorless liquid; 238 mg, 58%; IR
1
(CHCl3) ν 1744 cm-1 (C=O); H-NMR: δ 0.86-0.96 (6H, m, CH3), 1.25-1.50 (10H, m, CH2), 1.60-1.68
(4H, m, CH2), 4.10-4.16 (4H, m, CH2); MS (EI) m/z 215 (M+-1); [Calc. for C12H24O3: requires M,
216.1726. Found: 216.1722 (M+)].
Carbonic acid dibutyl ester (n-C4H9OCO2C4H9). A colorless liquid; 231 mg, 70%; IR (CHCl3) ν 1745
cm-1 (C=O); 1H-NMR: δ 0.88 (6H, t, J = 6.9 Hz, CH3), 1.20-1.40 (4H, m, CH2), 1.50-1.65 (4H, m, CH2),
4.05 (4H, t, J = 6.7 Hz, CH2); MS (EI) m/z 175 (M++1); [Calc. for C9H18O3: requires M, 174.1256.
Found: 174.1263 (M+)].
Formic acid benzyl ester [PhCH2OC(O)H]. A colorless liquid; 217 mg, 60%; IR (CHCl3) ν 1724 cm-1
(C=O); 1H-NMR: δ 5.12 (2H, s, CH2), 7.33-7.41 (5H, m, Ar), 8.14 (1H, s, CH); MS (EI) m/z 136 (M+);
[Calc. for C8H8O2, M 136.1749: requires C, 70.57; H, 5.92. Found: C, 70.12; H, 6.21].
References
1. For comprehensive reviews on organic carbonates, see: (a) Hegarty, A. F. In Comprehensive
Organic Chemistry; Sutherland, I. O., Ed; Pergamon: London, 1979; Vol. 2, p.1067. (b) Shaikh, A.
A. G; Sivaram, S. Chem. Rev., 1996, 96, 951.
2. Burk, R. M.; Roof, M. B. Tetrahedron Lett., 1993, 34, 395.
3. Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem., 1998, 63, 6031.
4. McGhee, W.; Riley, D. J. Org. Chem., 1995, 60, 6025.
5. Cella, J. A.; Bacon, S. W. J. Org. Chem., 1984, 49, 1122.
6. (a) Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl., 1987, 26, 894. (b) Burk, R. M.; Roof, M. B.
Tetrahedron Lett., 1993, 34, 395. (c) Bertolini, G.; Pavich, G.; Vergani, B. J. Org. Chem., 1998, 63,
6031.
7. (a) McGhee, W.; Riley, D. J. Org. Chem., 1995, 60, 6025. (b) Sakakura, T.; Saito, Y.; Okano, M.;
Choi, J.-C.; Sako, T. J. Org. Chem., 1998, 63, 7095. (c) Casadei, M. A,; Cesa, S.; Feroci, M.; Inesi,
A.; Rossi, L.; Moracci, F. M. Tetrahedron Lett., 1997, 53, 167. (d). Darensbourg, D. J.; Niezgoda, S.