Hydrochloric Acid → 4-(4-Phenoxyphenoxy)benzoic acid

HRID 1886499

Reaction equation

HRID 1886499 reaction equation
[O:1]([C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.O>[O:1]([C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19876201Methyl 4-(4-phenoxyphenoxy)benzoate

Product 1

HCID 108521644-(4-Phenoxyphenoxy)benzoic acidYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A slurry of 5.00 g (15.6 mmoles) of methyl 4-(4-phenoxyphenoxy)benzoate from Example A, 0.28 g (50.0 mmoles) of potassium hydroxide, 50 ml of methanol and 50 ml of deionized water is refluxed for 48 hours. Methanol is added until the mixture is homogeneous. Aqueous hydrochloric acid is added until the solution is strongly acidified, and the slurry is cooled. The resulting precipitate is filtered, washed with 300 ml of deionized water and dried in air. It is recrystallized from a minimum volume of hot 2-1 by volume methanol and water solution to yield 4.40 g (92 percent yield) of 4-(4-phenoxyphenoxy)benzoic acid having a melting point of 185° C. as measured by DSC.

Workup

  1. temperaturethe slurry is cooled
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with 300 ml of deionized water
  4. customdried in air
  5. customIt is recrystallized from a minimum volume of hot 2-1 by volume methanol and water solution

Sources & evidence

ORD record
ord-1363c0a98aec4abaa776dc70271a76e5
Source dataset
uspto-grants-1992_09
Patent number
US05151489

Linked notes

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