4-Aminophenol → Benzamide, N-(4-hydroxyphenyl)-

HRID 2233233Notes

Reaction equation

HRID 2233233 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(N(CC)CC)C.O>O1CCCC1>[C:1]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 962WaterHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 459327Benzamide, N-(4-hydroxyphenyl)-Yield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzoyl chloride (2.30 ml, 20.0 mmol) in tetrahydrofuran (25 ml) was added dropwise to a solution of 4-aminophenol (2.18 g, 20.0 mmol) and triethylamine (10 ml) in tetrahydrofuran (75 ml) at ambient temperature and the reaction allowed to stir for a further 18 hours. The reaction was poured into water and the solid material which formed was collected by suction filtration. Recrystallisation from ethyl acetate/isohexane (1:1), followed by solvent evaporation in vacuo, yielded N-benzoyl 4-hydroxyaniline (3.05 g, 72% yield) as a white solid:

Workup

  1. customthe solid material which formed
  2. filtrationwas collected by suction filtration
  3. customRecrystallisation from ethyl acetate/isohexane (1:1)
  4. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-811cc5c5a00646488df24616dd474c3e
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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