HCID 20827007, compound → HCID 22280028, compound

HRID 1591551Notes

Reaction equation

HRID 1591551 reaction equation
C(C1C=CC(COC2C=CC(CO)=CC=2)=CC=1)(C)(C)C.C[O:22][C:23](=[O:53])[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:44][CH:43]=3)=[CH:36][CH:35]=2)=[CH:28][C:27]=1[CH3:52]>>[C:48]([C:45]1[CH:46]=[CH:47][C:42]([CH2:41][O:40][C:37]2[CH:38]=[CH:39][C:34]([CH2:33][S:32][C:29]3[CH:30]=[CH:31][C:26]([O:25][CH2:24][C:23]([OH:53])=[O:22])=[C:27]([CH3:52])[CH:28]=3)=[CH:35][CH:36]=2)=[CH:43][CH:44]=1)([CH3:51])([CH3:49])[CH3:50]

Participants

3

Reactant 2

HCID 20827007HCID 20827007, compound2×HCID 22280136HCID 22280136, compound

Product 1

HCID 22280028HCID 22280028, compound

Procedure

Preparation of [4-(4-tert-Butyl-benzyloxy)-phenyl]-methanol (compound 34A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-tert-butyl-benzene and 4-hydroxymethyl-phenol. MS m/z 253 (M-OH). Step 2. Preparation of 4-tert-Butyl-1-(4-chloromethyl-phenoxymethyl)-benzene (compound 34B) The title compound was prepared in the manner analogous to Example 3B using 34A. MS m/z 253 (M-Cl). Step 3. Preparation of {4-[4-(4-tert-Butyl-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (compound 34C) The title compound was prepared in the manner analogous to Example 1F using 34B and 2C. MS m/z 465 (M+1). Step 4. Preparation of {4-[4-(4-tert-Butyl-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid (compound 34) The title compound was prepared in the manner analogous to Example 1 using 34C. mp 135-137° C.; IR (KBr) cm−1: 2961, 2908, 1751, 1495, 1233, 1194; 400 MHz 1H NMR (DMSO-d6): δ 13.00 (br(s), 1H), 7.27-7.38 (m, 4H), 7.02-7.17 (m, 4H), 6.82-6.88 (m, 2H), 6.69 (d, 1H, J=8.5 Hz), 4.96 (s, 2H), 4.61 (s, 2H), 3.99 (s, 2H), 2.08 (s, 3H), 1.22 (s, 9H); MS m/z 451 (M+1). Anal. Calc'd for C27H30O4S: C, 71.97; H, 6.71; found: C, 71.66; H, 6.52.

Workup

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

Sources & evidence

ORD record
ord-65803280bfaf469e83fe44c25bfb2185
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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