Water → 4-(Acetamidomethyl)benzoic acid

HRID 1451073Notes

Reaction equation

HRID 1451073 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C:12]([O-])(=[O:14])[CH3:13].[Na+].O>C(O)(=O)C>[C:12]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 655264-(Aminomethyl)Benzoic AcidHCID 517045Sodium Acetate

Product 1

HCID 5060644-(Acetamidomethyl)benzoic acidYield 72.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-aminomethylbenzoic acid (Aldrich, 1.51 g, 0.01 mol) and anhydrous sodium acetate (1.5 g, 0.018 mol) in glacial acetic acid (5 mL) was heated at reflux for 18 h. On cooling, the mixture was poured into cold water (50 mL). The precipitate was separated by filtration and washed several times with cold water. The cake was recrystallized from water to give 1.4 g (72.5%) of the title compound as a white powder, mp 195° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureOn cooling
  4. customThe precipitate was separated by filtration
  5. washwashed several times with cold water
  6. customThe cake was recrystallized from water

Sources & evidence

ORD record
ord-12f1e27cae5b4c7a9f2621ee04a97023
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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