Hydrochloric Acid → HCID 22279992, compound

Participants

Reaction Steps

A solution of {2-methyl-4-[2-(4′-trifluoromethyl-biphenyl-4-yl)-ethylsulfanyl]-phenoxy}-acetic acid methyl ester (0.78 g, 1.7 mmol) in 10 ml of tetrahydrofuran and 2.0 ml of water was treated with lithium hydroxide monohydrate (0.21 g, 5.0 mmol), and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with 5.0 ml of water and made strongly acidic by the addition of 4.0 N hydrochloric acid. The mixture was extracted with ethyl acetate (4×30 ml), and the combined extracts were washed with brine (2×50 ml), then dried over anhydrous sodium sulfate and concentrated. The crude product was recrystallized from ethyl acetate/hexane. mp 132-134° C.; IR (thin film) cm−1: 1741, 1709, 1490, 1326, 1239, 1110; 400 MHz 1H NMR (DMSO-d6) δ 7.82 (d, 2H, J=8.0 Hz), 7.74 (d, 2H, J=8.0 Hz), 7.61 (d, 2H, J=8.3 Hz), 7.31 (d, 2H, J=8.3 Hz), 7.15 (m, 2H), 6.75 (d, 1H, J=8.3 Hz), 4.64 (s, 2H), 3.11 (t, 2H, J=7.6 Hz), 2.82 (t, 2H, J=7.6 Hz), 2.12 (s, 3H); MS m/z 447 (M+1). Anal. Calc'd for C24H21F3O3S: C, 64.56; H, 4.74. found: C, 64.45; H, 4.58.

Provenance & Evidence