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

HRID 1086585Notes

Reaction equation

HRID 1086585 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 mmol) of methyl 4-(4-phenoxyphenoxy)benzoate from Example 30, 0.28 g (50.0 mmol) 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 homogenous. 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-7fb2e42b24cd4bac831a6e7bc78a78c5
Source dataset
uspto-grants-1991_07
Patent number
US05030706

Reaction notes

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