Hydrochloric Acid → 3-Amino-4-phenoxyphenol

HRID 1031650

Reaction equation

HRID 1031650 reaction equation
C(O)C.[N+:4]([C:7]1[CH:8]=[C:9]([OH:20])[CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-])=O.Cl>[Fe].O>[NH2:4][C:7]1[CH:8]=[C:9]([OH:20])[CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 130692153-Nitro-4-phenoxyphenol

Product 1

HCID 135148453-Amino-4-phenoxyphenolYield 82.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

120 ml of ethanol and 120 ml of water were added to 23.1 g of 3-nitro-4-phenoxyphenol, and the mixture was made into a solution by heating at 60° C. 2.3 ml of 4N hydrochloric acid was added thereto. While maintaining the reaction temperature at 65°-70° C., 16.8 g of an iron powder was added thereto in portions in 20 minutes. Stirring was conducted for 30 minutes at the same temperature. The reaction mixture was hot-filtered. 50 ml of water was added to the filtrate and the mixture was allowed to stand. The resulting crystal was collected by filtration to obtain 16.5 g (yield: 82.1%) of 3-amino-4-phenoxyphenol having a melting point of 156°-157° C.

Workup

  1. temperatureWhile maintaining the reaction temperature at 65°-70° C.
  2. waitwas conducted for 30 minutes at the same temperature
  3. filtrationThe reaction mixture was hot-filtered
  4. addition50 ml of water was added to the filtrate
  5. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-4f2250211d6a408ca486f923391cbdcc
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Linked notes

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