(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketone → 4-[4-(2-Butyl-benzofuran-3-carbonyl)-phenoxysulfonyl]-2-hydroxy-benzoic Acid

HRID 1067352Notes

Reaction equation

HRID 1067352 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].Cl[S:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([OH:36])[CH:28]=1)(=[O:26])=[O:25]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10]([C:11]1[CH:16]=[CH:15][C:14]([O:17][S:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([OH:36])[CH:28]=2)(=[O:26])=[O:25])=[CH:13][CH:12]=1)=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 96670(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketoneHCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 101414254-[4-(2-Butyl-benzofuran-3-carbonyl)-phenoxysulfonyl]-2-hydroxy-benzoic AcidYield 11%

Procedure

The title compound was prepared according to the procedure in Example 4 using commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (1.00 g, 3.40 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.61 g, 6.79 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with EtOAc/hexane gave 0.185 g (11%) of the title compound as an off white solid, mp 143-145° C. 1H NMR (DMSO-d6) δ0.76 (t, 3H), 1.12-1.22 (m, 2H), 1.60 (quintet, 2H), 2.69 (t, 2H), 7.21-7.38 (m, 7H), 7.61 (d, 1H), 7.76 (d, 2H), 7.98 (d, 1H). IR (KBr) 2950, 1690, 1600, 1380 and 1150 cm−1. mass spectrum (+ESI) m/z 495 (M+H). Anal. Calcd. for C26H22O8S.0.2H2O: C, 62.24; H, 4.58; N, 0.00. Found: C, 62.38; H, 4.59; N, 0.13.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-e65326e632884832aec67bc69eba9189
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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