Hydrochloric Acid → 4-(Acetamidomethyl)benzoic acid

HRID 1282129Notes

Reaction equation

HRID 1282129 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.[OH-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>C(OCC)(=O)C>[C:14]([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:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 5060644-(Acetamidomethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(aminomethyl)benzoic acid (20.46 g) in ethyl acetate (100 ml) was added an aqueous solution (100 ml) of sodium hydroxide (12 g) and acetic anhydride (14 ml) was further added at 5-7° C. The reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was made acidic with 10% hydrochloric acid and extracted with ethyl acetate:ethanol (10:1). The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-yellow solid (27.2 g). The obtained solid was crystallized from ethyl acetate:ethanol (1:1, 500 ml) to give the title compound (16.7 g) as white crystals, m.p.=200-202° C.

Workup

  1. additionwas further added at 5-7° C
  2. extractionextracted with ethyl acetate:ethanol (10:1)
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-257ca632d48b4d0db94e84fbb1cd2275
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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