Methanone, (4-hydroxyphenyl)(4-methoxyphenyl)- → 2-Hydroxy-4-[4-(4-methoxy-benzoyl)-phenoxysulfonyl]-benzoic acid

HRID 1107934Notes

Reaction equation

HRID 1107934 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl[S:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([OH:31])[CH:23]=1)(=[O:21])=[O:20]>C1COCC1>[OH:31][C:24]1[CH:23]=[C:22]([S:19]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6](=[O:7])[C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)(=[O:21])=[O:20])[CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 186743Methanone, (4-hydroxyphenyl)(4-methoxyphenyl)-HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 98888072-Hydroxy-4-[4-(4-methoxy-benzoyl)-phenoxysulfonyl]-benzoic acidYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure in Example 4 using commercial 4-hydroxy-4'methoxybenzophenone (0.206 g, 0.903 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.427 g, 1.81 mmol) in THF (5 mL). Purification by preparative HPLC (C18, eluting with 60% CH3CN/H2O containing 0.1% TFA) and crystallization from EtOAc/hexane gave 0.21 g (54%) of the title compound as an off white solid, mp 73-75° C.; 1H NMR (DMSO-d6) δ 3.85 (s, 3H), 7.07 (d, 2H), 7.24 (d, 2H), 7.36-7.38 (m, 2H), 7.68-7.73 (m, 4H), 7.99 (s, 1 H). IR (KBr) 3400, 1700, 1650, 1000 and 1260 cm-1. mass spectrum (-ESI) m/z 427 (M-H).

Workup

  1. customThe title compound was prepared
  2. customPurification
  3. washby preparative HPLC (C18, eluting with 60% CH3CN/H2O containing 0.1% TFA) and crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-c02d3103a474405a905e0c47c5ecfdd7
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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