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

HRID 1591550Notes

Reaction equation

HRID 1591550 reaction equation
COC1C=CC(COC2C=CC(CO)=CC=2)=CC=1.C[O:20][C:21](=[O:49])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)=[CH:34][CH:33]=2)=[CH:26][C:25]=1[CH3:48]>>[CH3:47][O:46][C:43]1[CH:44]=[CH:45][C:40]([CH2:39][O:38][C:35]2[CH:36]=[CH:37][C:32]([CH2:31][S:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][CH2:22][C:21]([OH:49])=[O:20])=[C:25]([CH3:48])[CH:26]=3)=[CH:33][CH:34]=2)=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 126484214-[(4-Methoxyphenyl)methoxy]benzenemethanolHCID 20827029HCID 20827029, compound2×

Product 1

HCID 22280141{4-[4-(4-Methoxy-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid

Procedure

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.

Workup

  1. customwas prepared in the manner analogous to Example 3B

Sources & evidence

ORD record
ord-c43e9dec1100419fbb0ec5bca74bc637
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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