4-Aminophenol → ethyl N-(4-hydroxyphenyl)carbamate

HRID 2259258Notes

Reaction equation

HRID 2259258 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[OH-].[Na+].[CH2:11]([O:13][C:14](Cl)=[O:15])[CH3:12].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:11]([O:13][C:14]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=1)=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 24489Sodium Dithionite

Product 1

HCID 602288ethyl N-(4-hydroxyphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-aminophenol 33.36 g (0.3 mole) and 12 g NaOH were dissolved in 120 ml water and cooled to ice salt bath temperature. To the stirring solution, 24 ml ethylchloroformate were slowly added. A white precipitate was found. One gram sodium dithionite was added and mixed. The solid was filtered by suction and washed with cold water (50 ml). Recrystallization from hot water gave a crystalline powder, 48.3 g (89%), MP 120°-123°.

Workup

  1. temperaturecooled to ice salt bath temperature
  2. additionmixed
  3. filtrationThe solid was filtered by suction
  4. washwashed with cold water (50 ml)
  5. customRecrystallization from hot water
  6. customgave a crystalline powder, 48.3 g (89%), MP 120°-123°

Sources & evidence

ORD record
ord-9c8be16579e44df7a80ecc209edf1a82
Source dataset
uspto-grants-1995_12
Patent number
US05472981

Reaction notes

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