Ethanol → 2-Amino-4-(benzyloxy)phenol

HRID 280826Notes

Reaction equation

HRID 280826 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N+:9]([C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:13]=1[OH:26])([O-])=O.C(O)C>O>[NH2:9][C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:13]=1[OH:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 46066344-(Benzyloxy)-2-nitrophenol

Product 1

HCID 141698072-Amino-4-(benzyloxy)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium dithionite (174.11 g, 10 moles) in water (400 ml) was dropwise added to the nitrophenol ((a), 93.0 g, 0.38 mole) in refluxing ethanol. The resulting solution was refluxed for further 3 hours, then cooled at room temperature and filtered. The obtained solution was concentrated at a final volume of 100 ml; Water (100 ml) was added and the separated amine ((b), 72.0 g, 88%) was recovered as brown powder.

Workup

  1. temperatureThe resulting solution was refluxed for further 3 hours
  2. filtrationfiltered
  3. concentrationThe obtained solution was concentrated at a final volume of 100 ml
  4. additionWater (100 ml) was added
  5. customthe separated amine ((b), 72.0 g, 88%) was recovered as brown powder

Sources & evidence

ORD record
ord-7454690f601b4630adb7db2cb890038e
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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