Water → p-Acetamidobenzoic acid

HRID 1451057Notes

Reaction equation

HRID 1451057 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([O-])(=[O:13])[CH3:12].[Na+].O>C(O)(=O)C>[C:11]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 517045Sodium Acetate

Product 1

HCID 19266p-Acetamidobenzoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-aminobenzoic acid (Aldrich, 50.0 g, 0.365 mol) and anhydrous sodium acetate (35.0 g, 0.427 mol) in glacial acetic acid (150 mL) was heated to reflux for 15 h. The mixture was poured into cold water (1 L). The precipitate was separated by filtration and washed several times with cold water. The cake was dried in oven at 70° C. and recrystallized from 2:1 water:ethanol to give 43.0 g (68%) of the title compound as off-white flakes, mp 258° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 h
  3. customThe precipitate was separated by filtration
  4. washwashed several times with cold water
  5. customThe cake was dried in oven at 70° C.
  6. customrecrystallized from 2:1 water

Sources & evidence

ORD record
ord-19f5cf91e0ff49c3a1b01dd58a51a638
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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