Hydrochloric Acid → 4-(4-acetamidophenoxy)benzoic Acid

HRID 23375Notes

Reaction equation

HRID 23375 reaction equation
[Li+].[OH-].[C:3]([NH:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1)(=[O:5])[CH3:4].Cl>O1CCOCC1>[C:3]([NH:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22573305Methyl 4-(4-acetamidophenoxy)benzoate

Product 1

HCID 36510794-(4-acetamidophenoxy)benzoic AcidYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous LiOH (1M, 3.12 mL) is added to a suspension of methyl 4-(4-acetamidophenoxy)benzoate (445 mg, 1.6 mmol) in dioxane (6 mL). The reaction is stirred for 90 minutes at room temperature. Concentrated HCl (1.5 mL) is added to lower the pH to less than 6 and the resulting precipitate is collected by filtration. The filter cake is washed with water then dried to give 4-(4-acetamidophenoxy)benzoic acid (337 mg, 80%). MS for C15H13NO4 (ESI) (M−H)− m/z 270.

Workup

  1. filtrationthe resulting precipitate is collected by filtration
  2. washThe filter cake is washed with water
  3. customthen dried

Sources & evidence

ORD record
ord-f78bd7aff101474e966964d223457cfb
Source dataset
uspto-grants-2005_02
Patent number
US06852716B2

Reaction notes

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