4-[(4-Methoxyphenyl)methoxy]benzenemethanol → {4-[4-(4-Methoxy-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid

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Reaction Steps

Preparation of [4-(4-Methoxy-benzyloxy)-phenyl]-methanol (compound 33A) The title compound was prepared in the manner analogous to Example 14A using 1-chloromethyl-4-methoxy-benzene and 4-hydroxymethyl-phenol. MS m/z 227 (M-OH). Step 2. Preparation of 4-Methoxy-1-(4-chloromethyl-phenoxymethyl)-benzene (compound 33B) The title compound was prepared in the manner analogous to Example 3B using 33A. MS m/z 227 (M-Cl). Step 3. Preparation of {4-[4-(4Methoxy-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (compound 33C) The title compound was prepared in the manner analogous to Example 1F using 33B and 2C. MS m/z 439 (M+1). Step 4. Preparation of {4-[4(4-Methoxy-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid (compound 33) The title compound was prepared in the manner analogous to Example 1 using 33C. mp 150-152° C.; HPLC: area %=96.69, r.t.=2.93 min., γ=214 nm, mobile phase=acetonitrile/water with 0.10% TFA; IR (KBr) cm−1: 2929, 1728, 1707, 1513, 1491, 1225; 400 MHz 1H NMR (DMSO-d6): δ 12.98 (br(s), 1H), 7.27-7.23 (m, 2H), 7.02-7.16 (m, 4H), 6.81-6.91 (m, 4H), 6.69 (d, 1H, J=8.6 Hz), 4.91 (s, 2H), 4.61 (s, 2H), 3.99 (s, 2H), 3.69 (s, 3H), 2.08 (s, 3H); MS m/z 423 (M−1). Anal. Calc'd for C24H24O3S: C, 67.90; H, 5.70; found: C, 67.48; H, 5.59.

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