Sodium Hydroxide → 4-Phenoxybenzoic acid

HRID 1777569Notes

Reaction equation

HRID 1777569 reaction equation
[O:1]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O.O1CCOCC1>[O:1]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 607605Methyl 4-phenoxybenzoate

Product 1

HCID 751824-Phenoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-phenoxybenzoate (0.144 g; 0.630 mmol) was added to a mixture of NaOH in water (1 mL; 2M) and dioxane (1 mL) and stirred vigorously at room temperature overnight. The resulting mixture was concentrated in vacuo and extracted with dichloromethane. The aqueous layer was acidified with a 6N solution of hydrochloric acid in water. The precipitated product was collected by filtration to yield 0.136 g (quantitative) of the title compound as a white solid which was used without further purification.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionextracted with dichloromethane
  3. filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-36005583ec05445492e01fbdf3f59e27
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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