Citric Acid → 4-(Pyridin-2-yloxy)benzoic acid

HRID 1911159Notes

Reaction equation

HRID 1911159 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1.[Li+].[OH-].C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 9991408Methyl 4-(pyridin-2-yloxy)benzoate

Product 1

HCID 222620524-(Pyridin-2-yloxy)benzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 44b (430 mg, 1.87 mmol), LiOH (180 mg, 7.5 mmol), THF (3 mL), MeOH (3 mL), and H2O (3 mL) was stirred at room temperature for 4 h. Then the reaction mixture was acidified with 15% citric acid (10 mL). The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give 44c (350 mg).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7f607d22319a473590838b83eb91f780
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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