Oxidation of alcohols into esters
Russ.Chem.Bull., Int.Ed., Vol. 58, No. 2, February, 2009
307
nꢀHexyl hexanoate (2a) (cf. Ref. 20). IR, ν/cm–1: 1735
(CDCl ), δ: 129.26 (C(3), C(5)); 129.76 (C(2), C(6)), 134.49
3
1
(
1
O—C=O). H NMR (CDCl ), δ: 0.92 (t, 6 H, CH , J = 6.5 Hz);
(C(4)); 135.01 (C(1)), 192.50 (C=O).
3
3
.40 (m, 10 H, CH ); 1.68 (m, 4 H, CH ); 2.40 (t, 2 H,
Benzoic acid (5). IR, ν/cm–1: 1720 (C=O). 1H NMR
2
2
CH COO, J = 7.5 Hz); 4.15 (t, 2 H, CH OCO, J = 6.5 Hz).
(CDCl ), δ: 7.50 (m, 3 H, H(3), H(4), H(5)); 8.14 (d, 2 H,
H(2), H(6), J = 9.4 Hz) 11.20 (s, 1 H, COOH). C NMR
2
2
3
13
13
C NMR (CDCl ), δ: 13.98 (CH ); 14.01 (CH ); 21.98, 22.11,
3
3
3
2
6
4.70, 25.64, 29.01, 31.54, 31.62 (CH ); 34.51 (CH COO);
(CDCl ), δ: 129.98 (C(3), C(5)); 130.18 (C(2), C(6)), 131.08
(C(1)); 133.79 (C(4)); 172.18 (C=O).
2
2
3
+
4.32 (CH OCO); 174.81 (CO). MS, m/z: 201 [M + H] .
2
nꢀHeptyl heptanoate (2b) (cf. Ref. 21). IR, ν/cm–1: 1737
1
(O—C=O). H NMR (CDCl ), δ: 0.80 (t, 6 H, CH , J = 6.3 Hz);
This work was financially supported by the Russian
Foundation for Basic Research (Project No. 06ꢀ03ꢀ32579a)
and by the Council on Grants at the President of the
Russian Federation (Program for the State Support of
Leading Scientific Schools, Grant 2942.2008.3).
3
3
1
.36 (m, 14 H, CH ); 1.60 (m, 4 H, CH ); 2.31 (t, 2 H,
2
2
CH COO, J = 7.4 Hz); 4.11 (t, 2 H, CH OCO, J = 6.4 Hz).
2
2
13
C NMR (CDCl ), δ: 13.88 (CH ); 13.98 (CH ); 21.86, 22.85,
3
3
3
2
4.70, 25.67, 25.84, 28.63, 29.90, 31.02, 31.72 (CH ); 34.89
2
(
[
CH COO); 64.99 (CH OCO); 174.01 (CO). MS, m/z: 229
M + H] .
2 2
+
nꢀNonyl nonanoate (2c) (cf. Ref. 22). IR, ν/cm–1: 1743
1
References
(O–C=O). H NMR (CDCl ), δ: 0.85 (t, 6 H, CH , J = 6.5 Hz);
3
3
1
.33 (m, 22 H, CH ); 1.58 (m, 4 H, CH ); 2.36 (t, 2 H,
2
2
CH COO, J = 7.5 Hz); 4.15 (t, 2 H, CH OCO, J = 6.4 Hz).
2
2
13
C NMR (CDCl ), δ: 13.90 (CH ); 14.05 (CH ); 21.87, 22.70,
1. W. S. Trahanovsky, L. B. J. Young, J. Chem. Soc., 1965,
5777.
2. W. S. Trahanovsky, L. B. J. Young, P. M. Nave, Tetrahedron
Lett., 1969, 30, 2501.
3. W. S. Trahanovsky, J. R. Glimore, P. C. Heaton, J. Org.
Chem., 1973, 38, 760.
3
3
3
2
2
1
2.90, 24.68, 25.01, 25.87, 25.94, 28.70, 29.24, 29.33, 29.46,
9.54, 31.52 (CH ); 34.41 (CH COO); 64.22 (CH OCO);
2
2
2
+
74.11 (CO). MS, m/z: 285 [M + H] .
nꢀUndecyl undecanoate (2d) (cf. Ref. 23). IR, ν/cm–1: 1735
1
(O—C=O). H NMR (CDCl ), δ: 0.88 (t, 6 H, CH , J = 6.5 Hz);
3
3
1
.26 (m, 30 H, CH ); 1.64 (m, 4 H, CH ); 2.28 (t, 2 H,
4. P. S. Radhakrishnamurti, M. K. Mahanti, Indian J. Chem.,
1970, 8, 977.
5. L. Syper, Tetrahedron Lett., 1966, 27, 4493.
6. W. S. Trahanovsky, L. B. J. Young, J. Org. Chem., 1966,
31, 2033.
2
2
CH COO, J = 7.5 Hz); 4.05 (t, 2 H, CH OCO, J = 6.4 Hz).
2
2
13
C NMR (CDCl ), δ: 14.01 (CH ); 14.06 (CH ); 22.64, 22.70,
3
3
3
2
2
4.98, 25.90, 28.61, 29.01, 29.10, 29.40, 29.53, 29.70, 29.82,
9.95, 31.87 (CH ); 34.36 (CH COO); 64.36 (CH OCO); 173.99
2
2
2
+
(
CO). MS, m/z: 341 [M + H] .
7. T. Ho, C. Wong, Synthesis, 1973, 206.
4
ꢀMethylpentyl 4ꢀmethylpentanoate (2e) (cf. Ref. 24). IR,
8. G. I. Nikishin, E. P. Kaplan, N. I. Kapustina, Izv. Akad.
Nauk SSSR, Ser. Khim., 1975, 1434 [Bull. Acad. Sci. USSR,
Div. Chem. Sci. (Engl. Transl.), 1975, 24].
–
1
1
ν/cm : 1740 (O—C=O). H NMR (CDCl ), δ: 0.85 (m, 12 H,
3
CH ); 1.22 (m, 2 H, CH ); 1.55 (m, 6 H, CH, CH ); 2.27 (t,
3
2
2
2
H, CH COO, J = 7.5 Hz); 4.01 (t, 2 H, CH OCO, J = 6.5 Hz).
9. B. Rindon, B. Scolastico, J. Chem. Soc., B, 1971, 2238.
10. C. Briquet, C. Freppel, J.ꢀC. Richer, M. Zador, Canad.
J. Chem., 1974, 52, 3101.
11. G. I. Nikishin, S. S. Spektor, N. I. Kapustina, E. P. Kaplan,
Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 1664 [Bull. Acad.
Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1977, 26].
12. V. Nair, S. B. Panicker, L. G. Nair, T. G. George, A. Augustine,
Synlett, 2003, 156.
2
2
13
C NMR (CDCl , δ: 22.16, 22.42 (CH ); 26.47, 27.62, 29.26,
3
3
2
1
9.34, 31.96, 32.38, 33.74, 34.93 (CH, CH ); 64.64 (CH OCO);
2 2
+
74.19 (CO). MS, m/z: 201 [M + H] .
ꢀMethylpentyl 3ꢀmethylpentanoate (2f) (cf. Ref. 25). IR,
3
–
1
1
ν/cm : 1738 (O—C=O). H NMR (CDCl ), δ: 0.87 (m, 12 H,
CH ); 1.28 (m, 2 H, CH ); 1.49 (m, 6 H, CH, CH ); 2.31 (m,
2
3
3
2
2
13
H, CH COO); 4.11 (t, 2 H, CH OCO, J = 6.6 Hz). C NMR
2
2
(
3
1
CDCl ), δ: 22.16, 22.42 (CH ); 26.47, 27.62, 29.26, 29.34,
13. V. Nair, L. Balagopal, R. Rajan, J. Mathew, Acc. Chem.
Res., 2004, 37, 21.
3
3
1.96, 32.38, 33.74, 34.93 (CH, CH ); 64.64 (CH OCO);
2 2
+
73.58 (CO). MS, m/z: 201 [M + H] .
ꢀEthylhexyl 2ꢀethylhexanoate (2g) (cf. Ref. 26). IR,
14. V. Nair, A. Deepthi, Chem. Rev., 2007, 107, 1862.
15. G. I. Nikishin, N. I. Kapustina, E. D. Lubuzh, S. S. Spektor,
E. P. Kaplan, Izv. Akad. Nauk SSSR, Ser. Khim., 1980,
2607 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.),
1980, 29].
2
–
1
1
ν/cm : 1742 (O—C=O). H NMR (CDCl ), δ: 0.91 (m, 12 H,
CH ); 1.28 (m, 10 H, CH ); 1.60 (m, 7 H, OCH CH, CH );
3
3
2
2
2
2
.29 (m, 1 H, CHCOO); 3.98 (d, 2 H, OCH CH, J = 5.6 Hz).
2
1
3
C NMR (CDCl ), δ: 10.94, 11.83, 13.90, 13.99 (CH ); 22.60,
16. M. P. Doyle, L. J. Zuidema, T. R. Bade, J. Org. Chem.,
1975, 40, 1454.
3
3
2
2.95, 23.79, 25.49, 28.87, 29.62, 30.40, 31.82 (CH ); 38.73
2
(
2
CH); 47.41(CH); 66.23 (CH OCO); 176.62 (CO). MS, m/z:
17. H. L. Hintz, D. C. Johnson, J. Org. Chem., 1967, 32, 556.
18. S. E. Schaafsma, H. Steinberg, T. S. Do Boer, Recuel, 1966,
85, 73.
2
+
57 [M + H] .
1
2ꢀPropyltetrahydrofuran (3b) (cf. Ref. 22). H NMR (CDCl ),
3
δ: 0.90 (t, 3 H, CH , J = 7.1 Hz), 1.53 (m, 4 H, CH ), 1.60 (m,
19. S. Kanemoto, H. Tomioka, K. Oshima, H. Nozaki, Bull.
Chem. Soc. Jpn., 1986, 59, 105.
3
2
2
H, CH (3)), 1.92 (m, 2 H, CH (4)), 3.69 (m, 3 H, CH (5),
2 2 2
CH(2)).
20. N. I. Kapustina, L. L. Sokova, V. D. Makhaev, A. P. Borisov,
G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 2000, 1870
[Russ. Chem. Bull., Int. Ed., 2000, 49, 1842].
21. S. Bhar, S. K. Chaudhuri, Tetrahedron, 2003, 59, 3493.
Benzaldehyde (4). IR, ν/cm–1: 1700 (C=O). 1H NMR
(
CDCl ), δ: 7.50 (m, 3 H, H(3), H(4), H(5)); 7.90 (d, 2 H,
3
13
H(2), H(6), J = 7.0 Hz), 10.04 (s, 1 H, CHO). C NMR