2-Nitrophenol → (S)-methyl-4-(1-methylheptyloxy)-3-nitrobenzoate

Beteiligte Stoffe

Reaktionsschritte

Methyl 4-hydroxy-3-nitrobenzoate was coupled with (R)-2-octanol using the same procedure as that given for alkylation of phenol 9, Scheme I, to give (S)-methyl-4-(1-methylheptyloxy)-3-nitrobenzoate (Compound 23, Scheme IV, R1 =(S)--OCH(CH3)C6H13). The product was purified by flash chromatography with hexanes/ethyl acetate (95/5) as eluent affording a yellow liquid, Rf [hexanes/ethyl acetate 95/5]: 0.25; 1H-NMR (300 MHz, CDCl3): δ 0.82 (t, 3 H, J=7.1 Hz); 1.14-1.50 (m, 8 H); 1.34(d, 3 H, J=6.1 Hz); 1.60(m, 1 H); 1.75(m, 1 H); 3.87(s, 3 H); 4.57(m, 1 H); 7.06(d, 1 H, J=8.9 Hz); 8.11(dd, 1 H, J=2.2 Hz, J=8.9 Hz); 8.39(d, 1 H, J=2.2 Hz); 13C-NMR (300 MHz, CDCl3): δ 13.96, 19.31, 22.47, 25.06, 29.02, 31.60, 36.00, 52.35, 76.80, 114.63, 121.80, 127.17, 134.80, 140.27, 154.91, 165.08; Mass spectrum, m/z(rel.intensity): 309 (M+ 1), 197(32), 166(46), 112(48), 71(63), 57(100), 55(46).

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