Sodium Hydroxide → 2-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic Acid

HRID 1796683Notes

Reaction equation

HRID 1796683 reaction equation
C[O:2][C:3](=[O:24])[C:4]([CH3:23])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[CH3:5].[OH-].[Na+]>C1COCC1.CO>[CH3:23][C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)([CH3:5])[C:3]([OH:24])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 210251532-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic Acid Methyl Ester

Product 1

HCID 221794892-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic AcidYield 91%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 433A (5.05 g, 15.2 mmol) in a mixed solvent of THF/MeOH (45 ml, 2/1) was added 2N NaOH (15.2 ml, 30.4 mmol). The mixture was stirred at rt for 2.5 h, concentrated. The residue was purified by flash chromatography on silica gel (2%-5% MeOH—CH2Cl2) gave 433B (4.38 g, 91%) as a light yellow solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on silica gel (2%-5% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-9362d0243dfb4a1fab8007fcd86b416d
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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