Phenol → 2-Methoxy-5-phenoxysulfonylbenzoic acid

HRID 1683184Notes

Reaction equation

HRID 1683184 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-:23].[Na+]>O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12]([O:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:23])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 1040075-Chlorosulphonyl-2-anisic acid

Product 1

HCID 190429722-Methoxy-5-phenoxysulfonylbenzoic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a rapidly stirred mixture of 2-methoxy-5-chlorosulfonylbenzoic acid (5.0 g, 20 mmol) and phenol (1.88 g, 20 mmol) in water (100 mL) was added dropwise a solution of sodium hydroxide (16 mL, 10%; 40 mmol) over 10 min. The mixture was stirred for 18 h, and then extracted with ether. The aqueous phase was acidified to pH 1 with cone. HCl and the white precipitate filtered off to give the title compound (4.05 g).

Workup

  1. extractionextracted with ether
  2. filtrationHCl and the white precipitate filtered off

Sources & evidence

ORD record
ord-37e9e2a71b764672be4deb3af1c78e72
Source dataset
uspto-grants-1997_06
Patent number
US05637600

Reaction notes

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