Ethanol → 2-Amino-4-(benzyloxy)phenol

HRID 34702Notes

Reaction equation

HRID 34702 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-da08935f8bd547d49b67bfa3a6309bd2
Source dataset
uspto-grants-1988_08
Patent number
US04762925

Reaction notes

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