Reaction Steps
The benzoyl ester of (S)-4'-(1-methylheptyloxy)-3'-nitro-4-biphenylylbenzoate was saponified using the same procedure as that used for saponification of (S)-[4-(1-methylheptyloxy)-3-nitrophenyl]-benzoate except that the reaction was carried out at 60° C. to give (S)-4'-(1-methylheptyloxy)-3'-nitro-4-hydroxybiphenyl (Compound 17, Scheme II, R2 =(S)--OCH(CH3)C6H13) as a very viscous orange liquid after flash chromatography with hexanes/ethyl acetate [88/12]; Rf [hexanes/ethyl acetate 85/15]: 0.17; 1H NMR (300 MHz, CDCl3): δ0.86(t, 3H, J=6.6 Hz), 1.18-1.52(m, 8H), 1.35(d, 3H, J =6.1 Hz), 1.62(m, 1H), 1.78(m, 1H), 4.50 (m, 1H), 5.22(broad s, 1H), 6.89(d, 2H, J=8.5 Hz), 7.07 (d, 1H, J=8.8 Hz), 7.39 (d, 2H, J=8.5 Hz), 7.62(dd, 1H, J =2.4 Hz, J=8.8 Hz), 7.92 (d, 1H, J=2.4 Hz); 13C NMR (300 MHz, CDCl3): δ13.99, 19.49, 22.50, 25.19, 29.10, 31.65, 36.17, 76.57, 115.94, 116.17, 123.30, 127.99, 131.21, 131.64, 133.09, 141.00, 15.42, 155.52; IR (CHCl3); 350, 3300(broad), 3020, 2920, 2840, 1610, 1540, 1510, 1485, 1350, 1260, 1220, 1160, 1110, 1040, 925, 825 cm-1 ; Mass spectrum, m/z(rel.intensity): 343(M+ 5), 231(100), 185(6), 57(6), 43(12).
