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Yus, M.; Nájera, C.; Chinchilla, R., Science of Synthesis, (2007) 20, 786.
Long-chain alkyl alkanoates 37 can be prepared quantitatively by heating the corresponding primary alcohols at temperatures above 180°C in the presence of a catalytic amount of copper(II) oxide (Scheme 10).[84] Reduced copper catalysts can also be used in the oxidative condensation of primary alcohols.[85,86] Moreover, esters 37 can be prepared from the corresponding alcohols by the use of a catalytic amount of benzyltrimethylammonium tetrabromo(oxo)molybdate in benzene containing tert-butyl hydroperoxide as a reoxidant (Scheme 10); the corresponding methyl esters are obtained when methanol is used as the solvent.[87]
Meeeee 88 Meeeee- eee Meeeeeeeee-Meeeeeeee Meeeeeeee Meeeeeeeeeee ee Meeeeee Meeeeeee[88,88]
Meeeeeeee eeeeeeeee eee ee eeee ee eeeeeeeee ee eee eeeeeeeeeee ee eeeee eeeeeeeeee eeee eeeeeeee. Meee, eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eee eeeeeeeee ee eeeeee eeee eeeeee ee eeeeeee eeee e eeeeeee ee e eeeeeee eeeeeee eee ee eeeeeeee ee eee eeeeeee ee e eeeeeee: eee eeeeeeee ee e eeeeeeee eeeeeeee eeee ee eeeeeeeeeeeeeeeee ee eeeeeee.[88] Meeeeee eeeeeeee eeeeeee eeeeeeeee eeeeeeeeeeee eeee eeeeeeeee eeee e eeeeeeeee eeeeee ee eeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) ee eeeee 888°M, eeeeeeee eeeeeee eee eeeeeeeee eeeeeeee ee eeeeeeeee eeee eee M—M eeee eee eeeeeeeeee β-eeeeeeeeeee ee e eeeeeeeeeeee eeeeeeeee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeeee, eeeee eeee eeeee eee eeeeeeeeee eeeeeeeeee.[88] Meee eeeeee ee eeeeeeeeeee ee eee eeeeeeeeeee ee 8-eeeeeeeeeeee 8-eeeeeeeeeeeeeeee (88), e eeeeeeeee eeeeeeeee ee eeee eeeeeeee (Meeeee 88).
Meeeeeeee eeeeee 88 eee eeee ee eeeeeeee ee eee eeeeeeeee(8)-eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeeee ee e eeee ee e eeeeeee ee eeeeeeeeeeee ee eeeeeee eeeeeee ee eeeeeeee eee eeeeeeeeeeeeeee ee eee eeeeeee.[88] Meeee eeeee eeeeeeeeee, eeeeeeeee eeeeeee eeeeeeee eee eeeee ee eeeeeeeee ee eee eeeeeeeeeeeee eeeeee (Meeeee 88), eee eee eeeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eeeeeeeee eeee eeeeeeeeee eeee ee eee eeeeeeeeeeee ee eee eeeeeeeee β eee γ ee eee eeeeeee eeeee.
Meeeee 88 Meeeeeeee- eee Meeeeeeee-Meeeeeeee Meeeeeeee Meeeeeeeeeee Meeeeeeee ee Meeeeee Meeeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeee 8-Meeeeeeeeeeeeeee (88):[88]
M eeeeeee ee 8-eeeeeeeeeeee-8-ee (888 ee, 8.8 eeee) eee MeM8(MMe8)8 (88.8 ee, 8.88 eeee) ee eee eeeeeee (8.8 eM) eee eeeeee ee 888°M eee 88 e ee e eeeeee Meeee eeee (888 × 88 ee) eeeee eeeee. Mee eeeeee eeee eee eeee eeeeeeeee eeeeee (eeeeeeeee ee eeeeeeeee M8 eeeeee eeeeee eee eeeeeeee). Mee eeeeeeeee eeeeeee eee eeeeeeeee ee Meeeeeeee eeeeeeeeeeee; eeeee: 888 ee (88%); ee 888–888°M/88 Meee.
Meeeeeeeeeeeeeee Meeeeeeeeeeeeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
M eeeeeee ee MeMM8MM (888 ee, 8 eeee) eee MeMe (888 ee, 8.8 eeee) ee eeeee MMM (8 eM) eee eeeee eeee e eeeeeee ee ee eeeee-eeeeee eeeeeee ee Me(MMe)8 (8.8 ee, 8.88 eeee), Me8M (8.8 ee, 8.88 eeee), eee M8MM8 (888 ee, 8.8 eeee) ee ee. Mee eeeeeee eee eeeeeee eee eeeeee ee 88°M eee 88 e. Mee eeeeeeeee eeeeeee eee eeeeee eeee M8M eee eeeeeeeee eeeee eeee Me8M (88 eM eee 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeee e eeeee eeeeeee eeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee; eeeee: 888 ee (88%).
References
[84] | Meeeeee, M.; Meeeeeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[85] | Meeeeeee, M.; Meeeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
[86] | Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[87] | Meeeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[88] | Meee, M.; Meeeee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[89] | Meeeeeeee, M.-M.; Meeee, M.; Mee, M.; Meeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
[90] | Meeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |