Hydrochloric Acid → HCID 54040210, compound

Participants

Reaction Steps

To a solution of 5.3 mmol of ester 10 in 40 ml of methanol and 15 ml of water, 22 mmol of LiOH·H2O was added. The reaction mixture was stirred vigorously at room temperature for 14-22 h until no starting material was detected by TLC. The solution was diluted with 65 ml of 3.5% (wt/wt) NaOH solution, acidified by adding concentrated HCl with ice and extracted several times with ethyl ether. The combined organic layers were dried over anhydrous MgSO4 and the solvent removed. The phenol were purified by flash chromatography with hexanes/ethyl acetate [90:10] to give (S)-4-(1-methyl-heptyloxy)-3-nitro-phenol (Compound 11, Scheme I, R2 =(S)-OCH(CH3)C6H13) in 89-98% yield as an orange liquid: Rf [hexanes/ethyl acetate 85/15]: 0.24; 1H NMR (300 MHz, CDCl3): δ 0.84(t, 3H, J=6.8 Hz), 1.16-1.48(m, 8H), 1.27(d, 3H, J=6.1 Hz), 1.56(m, 1H), 1.72(m, 1H), 4.35(m, 1H), 5.44(broad s, 1H), 6.94(d, 1H, J=9 Hz), 7.01(dd, 1H, J=2.8 Hz, J=9 Hz), 7.28(d, 1H, J=2.8 Hz); 13C NMR (300 MHz, CDCl3): δ 13.98, 19.49, 22.50, 25.19, 29.15, 31.66, 36.19, 77.57, 112.03, 118.50, 121.44, 140.98, 145.81, 148.84; Mass spectrum, m/z(rel.intensity): 267(M+ 0.3), 156(8), 155(100), 71(9) 57(20), 55(16), 43(29).

Provenance & Evidence