Hydrochloric Acid → 4-Amino-3-methoxyphenol

HRID 1885189Notes

Reaction equation

HRID 1885189 reaction equation
S(O)(=O)(C1C=CC([NH2:9])=CC=1)=O.C(=O)([O-])[O-].[Na+].[Na+].N([O-])=O.[Na+].Cl.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:9][C:30]1[CH:29]=[CH:28][C:27]([OH:31])=[CH:26][C:25]=1[O:24][CH3:23]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 8479Sulfanilic acidHCID 90073-MethoxyphenolHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 23668193Sodium Nitrite

Product 1

HCID 198180564-Amino-3-methoxyphenolYield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Sulphanilic acid (43.3 g) and anhydrous sodium carbonate (13.25 g) were dissolved in water (250 ml) and cooled to 15 C. Sodium nitrite (18.5 g) in water (100 ml) was added and the mixture was immediately poured onto a mixture of ice (300 ml) and hydrochloric acid (54 ml), and stirred at 0° for 20 minutes. The suspension was then added to a cooled solution of 3-methoxyphenol (31 g) and sodium hydroxide (55 g) in water (300 ml). The resulting deep red solution was stirred for 1 hour then heated to 70°. Sodium dithionite was added portionwise until the colour discharged on cooling, crystals of 4-amino-3-methoxyphenol (23 g, 66%) formed which were filtered, washed with water and dried, m.p. 168°-170°.

Workup

  1. temperaturecooled to 15 C
  2. stirringThe resulting deep red solution was stirred for 1 hour
  3. temperaturethen heated to 70°
  4. temperatureon cooling

Sources & evidence

ORD record
ord-71e6012b82c44edc8ae74fcaadd684e9
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

Loading…