Sulfuric Acid → HCID 9835091, compound

Participants

Reaction Steps

2-Ethyl-1-hexanol (21.0 g, 0.161 mol), 2-mercaptobenzoic acid (25.0 g, 0.162 mol), toluene (200 mL), and concentrated sulfuric acid (0.2 mL) were placed in a 500-mL three-neck round-bottom flask equipped with a magnetic stirring bar, a water separator, and a reflux condenser. After the mixture had been heated under reflux with stirring for 6 h, the solid 2-mercaptobenzoic acid had disappeared, and 2.90 mL (0.161 mol) of water had been collected by the water separator. The mixture was allowed to cool to room temperature and washed in succession with 20 mL of saturated NaHCO3 solution and two 50-mL portions of brine. Then the organic layer was dried over anhydrous MgSO4 and freed of solvent by rotary evaporation under vacuum to give 40.9 g (95%) of residual 2-ethylhexyl 2-mercaptobenzoate as a mobile straw-colored oil; 1H NMR (400 MHz, in CDCl3 w/TMS, ppm) 0.88-0.97 (m, 6H, 2CH3), 1.3-1.5 (m, 8H, 4CH2), 1.68-1.78 (m, 1H, CH), 4.21-4.29 (m, 2H, OCH2), 4.73 (s, 1H, SH), 7.1-7.3 [m, 3H, H-4 and H-5 with d (J=3.2 Hz) for H-3 at 7.29], 8.01 (d, J=7.6 Hz, H-6); {1H}13C NMR (100 MHz, in CDCl3 w/TMS, ppm) 166.99 (C═O), 138.49 and 126.39 (C-1 and C-2), 132.53, 131.77, 131.12, and 124.82 (C-3, -4, -5, and -6), 67.86, 39.19, 30.92, 29.33, 24.34, 23.35, 14.44, and 11.46 (8 aliphatic Cs).

Provenance & Evidence