Sodium Hydroxide → HCID 61395548, compound

HRID 1422840Notes

Reaction equation

HRID 1422840 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)[CH:5]=1.[OH-].[Na+]>CO.C1COCC1.O>[Cl:17][C:16]1[C:11]([O:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:19])=[O:2])=[N:12][CH:13]=[C:14]([Cl:18])[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67380717HCID 67380717, compound

Product 1

HCID 61395548HCID 61395548, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 3-(3,5-dichloro-pyridin-2-yloxy)-benzoic acid methyl ester (1100 mg, 4.0 mmol) and NaOH (700 mg, 16 mmol) in methanol:THF:water (1:1:1, 6 mL) was stirred at room temperature for 8 h. Solvents were evaporated. Crude mass was taken in water (40 mL), acidified to pH 4.0 and extracted with ethyl acetate. Evaporation of ethyl acetate yielded 3-(3,5-dichloro-pyridin-2-yloxy)-benzoic acid (908 mg).

Workup

  1. customSolvents were evaporated
  2. extractionextracted with ethyl acetate
  3. customEvaporation of ethyl acetate

Sources & evidence

ORD record
ord-aa7c3a3f548443a2a6d2fbcb640250ed
Source dataset
uspto-grants-2015_01
Patent number
US08927549B2

Reaction notes

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