Water → 3-Amino-2,6-dimethylphenol

HRID 258958

Reaction equation

HRID 258958 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[OH:12].O.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].C(O)(=O)C>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([OH:12])[C:4]([CH3:11])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 814763-Nitro-2,6-xylenol

Product 1

HCID 814773-Amino-2,6-dimethylphenolYield 62%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

157 g (0.94 mole) of 2,6-dimethyl-3-nitro phenol is added little by little, while stirring, to a reducing mixture consisting of 950 cm3 of water, 30 cm3 of acetic acid and 158 g of iron, which has first been heated to 70°. When this addition has been completed, the heating is continued for 20 minutes. The reaction mixture is then neutralized with sodium carbonate and the boiling liquid is filtered. After cooling the filtrate, drying yields 80 g of 3-amino-2,6-dimethyl phenol which, after recrystallization in benzene, melts at 104°.

Workup

  1. temperaturehas first been heated to 70°
  2. additionWhen this addition
  3. filtrationthe boiling liquid is filtered
  4. temperatureAfter cooling the filtrate
  5. customdrying

Sources & evidence

ORD record
ord-8ba5f60dc77743459513b68ac7f17a38
Source dataset
uspto-grants-1977_07
Patent number
US04035422

Linked notes

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