Sodium Hydroxide → 4-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid

HRID 433040Notes

Reaction equation

HRID 433040 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[C:9]([OH:11])[C:8]([Br:12])=[C:7]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH:6]=1)C.[OH-].[Na+]>C(O)C.O>[Br:12][C:8]1[C:9]([OH:11])=[CH:10][C:5]([C:4]([OH:24])=[O:3])=[CH:6][C:7]=1[O:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 574196834-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid ethyl ester

Product 1

HCID 220524124-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acidYield 31%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 25.6 g (59 mmol) of 4-bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid ethyl ester in 300 ml of ethanol and 2.36 g (65 mmol) of sodium hydroxide in 15 ml of water was stirred at room temperature for 12 h. The solvent was removed and the residue was distributed between water and ethyl acetate. The aqueous solution was acidified with 1 N HCl and the precipitate was filtered to give 4.35 g (31%) of the title compound.

Workup

  1. customThe solvent was removed
  2. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-d1ddc7a20b934bdfad62c304f6bf8961
Source dataset
uspto-grants-2003_12
Patent number
US06664393B2

Reaction notes

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