Sulfuric Acid → 3-Amino-2,4-dimethylphenol

HRID 579972

Reaction equation

HRID 579972 reaction equation
C([NH:4][C:5]1[C:6]([CH3:13])=[C:7]([OH:12])[CH:8]=[CH:9][C:10]=1[CH3:11])(=O)C.S(=O)(=O)(O)O>C(O)C>[NH2:4][C:5]1[C:6]([CH3:13])=[C:7]([OH:12])[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10419764N-(3-Hydroxy-2,6-dimethylphenyl)acetamide

Product 1

HCID 141306083-Amino-2,4-dimethylphenolYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g of 3-acetamido-2,4-dimethylphenol (55.9 mmol), 250 ml of concentrated sulfuric acid and 200 ml of ethanol was refluxed for 30 minutes and, then, concentrated under reduced pressure. The residue was dissolved in water and the solution was made alkaline with ammonia water and extracted with ether. The ether layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate (dehydration) and concentrated under reduced pressure. The residue was recrystallized from ethanolhexane to give 5.3 g (69%) of the title compound as colorless plates, m.p. 177°-179° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ether
  5. washThe ether layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate (dehydration)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethanolhexane

Sources & evidence

ORD record
ord-0564bda8e7404383b919e8d4ec3a662c
Source dataset
uspto-grants-1988_06
Patent number
US04751232

Linked notes

Loading…