{4-[(2,4-dichlorobenzyl)oxy]phenyl}methanol → HCID 22280008, compound

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Reaction Steps

Preparation of [4-(2,4-Dichloro-benzyloxy)-phenyl]-methanol (compound 32A) The title compound was prepared in the manner analogous to Example 14A using 2,4-dichloro-1-chloromethyl-benzene and 4-hydroxymethyl-phenol. MS m/z 265 (M-OH). Step 2. Preparation of 2,4-Dichloro-1-(4-chloromethyl-phenoxymethyl)-benzene (compound 32B) The title compound was prepared in the manner analogous to Example 3B using 32A. MS m/z 265 (M-Cl). Step 3. Preparation of {4-[4-(2,4-Dichloro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (compound 32C) The title compound was prepared in the manner analogous to Example 1F using 32B and 2C. MS m/z 477 (M+1). Step 4. Preparation of {4-[4-(2,4-Dichloro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid (compound 32) The title compound was prepared in the manner analogous to Example 1 using 32C. mp 143-145° C.; IR (KBr) cm−1: 3062, 2936, 1724, 1492, 1227, 1192; 400 MHz 1H NMR (DMSO-d6): δ 12.97 (br(s), 1H), 7.64 (d, 1H, J=2.0 Hz), 7.54 (d, 1H, J=8.3 Hz), 7.42 (dd, 1H, J=8.3, 2.0 Hz), 7.01-7.20 (m, 4H), 6.84-6.92 (m, 2H), 6.69 (d, 1H, J=8.5 Hz), 5.05 (s, 2H), 4.62 (s, 2H), 4.01 (s, 2H), 2.08 (s, 3H); MS m/z 461 (M−1). Anal. Calc'd for C23H20Cl2O4S: C, 59.62; H, 4.35; found: C, 59.33; H, 4.28.

Provenance & Evidence