Sodium Hydroxide → 3-Phenoxybenzoic acid

HRID 1777573Notes

Reaction equation

HRID 1777573 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([O:13]CC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O.O1CCOCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15674478Ethyl 3-phenoxybenzoate

Product 1

HCID 195393-Phenoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-phenoxybenzoate (0.220 g; 0.725 mmol) was added to a mixture of NaOH in water (1.5 mL; 2M) and dioxane (1.5 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 0.200 g (quantitative) of the title compound as a white solid which was used without further purifications.

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-577aa10df5d14c14beca4810a9be7bcc
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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