Hydrochloric Acid → Phenol, 4-methoxy-2-nitro-

HRID 268261Notes

Reaction equation

HRID 268261 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1N)[O:7][CH3:8])([O-:3])=[O:2].[OH-:13].[K+].Cl>O>[N+:1]([C:4]1[CH:5]=[C:6]([O:7][CH3:8])[CH:9]=[CH:10][C:11]=1[OH:13])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 15285Phenol, 4-methoxy-2-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 168 g. (0.93 m.) of 3-nitro-p-anisidine, 130 g. of KOH and 1500 ml. of H2O was refluxed with stirring overnight. The solution was acidified with conc. HCl, keeping the temperature below 20°C. The crude product was collected by filtration washed with H2O and air-dried to give 279 g. m.p. 74°-76°C. A recrystallization from 2000 ml. of ethanol yields 106 g. m.p.76°-78°C.

Workup

  1. additionA mixture of 168 g
  2. customthe temperature below 20°C
  3. filtrationThe crude product was collected by filtration
  4. washwashed with H2O
  5. customair-dried
  6. customto give 279 g
  7. customA recrystallization from 2000 ml
  8. customof ethanol yields 106 g

Sources & evidence

ORD record
ord-737cbfa9255642b9b0da869191dea83b
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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