Hydrochloric Acid → HCID 54015350, compound

Participants

Reaction Steps

To a solution of 1.086 g (3.89 mmol) of (S)-4-(1-methylheptyloxy)-2-nitrobenzaldehyde in 40 ml of acetone was added a solution of KMnO4 (0.984 g, 6.23 mmol) in 47 ml of water dropwise. The reaction mixture was stirred at room temperature for 6 h and then treated with 5% Na2SO3 (100 ml), acidified with conc. HCl (pH: 4-5), and the resulting solution was extracted with ethyl ether several times. The organic extract was concentrated and extracted with 10% NaOH solution. The alkaline extract was washed with ether, acidified with conc. HCl/ice, and the resulting solution extracted with ethyl ether. The organic layer was washed with water, dried, and the solvent evaporated. (S)-4-(1-Methylheptyloxy)-2-nitrobenzoic acid (Compound 37, Scheme VI, R1 =(S)--OCH(CH3)C6H13) was obtained as a dark orange liquid (0.8 g, 70% ) which was used in the next step without further purification; Rf [hexanes/ethyl acetate 70/30+1 drop of acetic acid]: 0.16; 1H NMR (300 MHz, CDCl3): δ 0.86(t, 3 H, J=6.8 Hz), 1.16-1.48(m, 8 H), 1.32(d, 3 H, J=5.(Hz), 1.60(m, 1 H), 1.72(m, 1 H), 4.45(m, 1 H), 7.02(dd, 1 H, J=2.4 Hz J=8.8 Hz), 7.09(d, 1 H, J=2.4 Hz) , 7.90(d, 1 H, J=8.8 Hz); 13C NMR (300 MHz, CDC3): δ 13.98, 19.22, 22.51, 25.24, 29.14, 31.68, 36.14, 79.94, 110.26, 117.84, 118.98, 132.97, 150.69, 160.61, 170.81; Mass spectrum, m/z(rel.intensity): 295(M+ 1), 265(9), 166(8), 135(36), 112(14), 71(66), 57(100), 55(27), 43(94), 41(69).

Provenance & Evidence