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

HRID 1591549Notes

Reaction equation

HRID 1591549 reaction equation
ClC1C=C(Cl)C=CC=1COC1C=CC(CO)=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]([Cl:46])=[CH:42][C:41]=3[Cl:47])=[CH:34][CH:33]=2)=[CH:26][C:25]=1[CH3:48]>>[Cl:47][C:41]1[CH:42]=[C:43]([Cl:46])[CH:44]=[CH:45][C:40]=1[CH2:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][S:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:22][C:21]([OH:49])=[O:20])=[C:25]([CH3:48])[CH:26]=2)=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 2763433{4-[(2,4-dichlorobenzyl)oxy]phenyl}methanolHCID 20827020HCID 20827020, compound2×

Product 1

HCID 22280008HCID 22280008, compound

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-75020e9d795e4bae98f0cf7d7c2a177e
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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