p-Toluenesulfonic acid → HCID 12150663, compound

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Reaction Steps

A mixture of p-toluenesulfonic acid (130 mg, 0.75 mmol) and 2-{[4-(4-hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-hydrazono}-propionic acid ethyl ester (193 mg, 0.50 mmol) in toluene (2 mL) was heated to reflux for 2 hours and then cooled to room temperature. Saturated aqueous NaHCO3 (10 mL) and ehtyl acetate (25 mL) were added. The organic layer was separated, washed with saturated NaHCO3 (2 times 25 mL), 1M hydrochloric acid (25 mL), brine (25 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative thin layer chromatography (3% methanol in methylene chloride ) to afford the title compound (60 mg) as a solid. 1H NMR (400 MHz, CDCl3) δ8.82 (s, 1H), 7.20 (s, 1H), 7.09 (s, 1H), 6.74 (d, 1H), 6.55 (d, 1H), 6.28-6.25 (m, 1H), 4.41-4.35 (q, 2H), 3.15-3.11 (m, 1H), 2.30 (s, 3H), 2.20 (s, 3H), 1.40 (t, 3H), 1.18 (d, 6H). MS (APCI−) Calc: 367.2, Found: 366.3 (M−1).

Provenance & Evidence