Reaction Steps
4-Methyl-3-nitrophenol (Compound 33, Scheme VI) was coupled with (R)-2-octanol using the same procedure as that given for alkylation of phenol 9, Scheme I, to give (S)-4-(1-methylheptyloxy)-2-nitro-toluene (Compound 34, Scheme VI, R1 =(S)--OCH(CH3)C6H13) as a yellow liquid; Rf [Hexanes/ethyl acetate 99/1]: 0.26; 1H NMR (300 MHz,CDCl3): δ 0.87(t, 3 H, J=6.6 Hz), 1.16-1.65(m, 12 H), 1.70(m, 1 H), 2.50(s, 3 H), 4.37(m, 1 H), 7.02(dd, 1 H ,J=2.7 Hz, J=8.5 Hz), 7.19(d, 1 H, J=8.5 Hz), 7.47(d, 1 H, J=2.7 Hz); 13C NMR (300 MHz, CDCl3): δ 13.97, 19.41, 19.63, 22.51, 25.32, 29.14, 31.69, 36.20, 74.72, 111.05, 121.44, 125.12, 133.44, 149.5, 156.77; IR (CHCl3): 3020, 2940, 2850, 1620, 1550, 1525, 1490, 1375, 1300, 1240, 1220, 1110, 1050, 975, 860, 825 cm-1 ; Mass spectrum, m/z(rel.intensity): 265(M+ 11), 153(33), 136(100), 112(21), 71(40), 57(70), 51(11), 43(78), 41(66).
