Sodium Hydroxide → {4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic acid

HRID 984944Notes

Reaction equation

HRID 984944 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)=[C:8]([Cl:30])[CH:7]=1)C.[OH-].[Na+]>C1COCC1.C(O)C>[Br:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:23]2[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=2)=[CH:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:31])=[O:3])=[CH:7][C:8]=2[Cl:30])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10120503{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic Acid Ethyl Ester

Product 1

HCID 10230466{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic acidYield 84.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[3,3-bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic acid ethyl ester (example 9) (1.0 g, 1.8 mmol) in THF (8 ml) and ethanol (5 ml) was added 1N NaOH (4.0 ml) and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was concentrated in vacuo. The residue was suspended in water and 817 mg (82%) of the title compound was isolated by filtration as the sodium salt.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-143faa6541164b22a38a6939edc9c97e
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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