Acetic Acid → 2-Amino-4-chloro-5-methylphenol

HRID 1741545

Reaction equation

HRID 1741545 reaction equation
O.C(O)C.C(O)(=O)C.[Cl:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[C:12]([N+:18]([O-])=O)[CH:11]=1.CC(C)=O>[Fe].CCCCCC.C(OCC)(=O)C>[NH2:18][C:12]1[CH:11]=[C:10]([Cl:9])[C:15]([CH3:16])=[CH:14][C:13]=1[OH:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 235324-Chloro-5-methyl-2-nitrophenolHCID 19096565Water ethanol

Product 1

HCID 1045242-Amino-4-chloro-5-methylphenolYield 43%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To 15 ml of a solvent mixture of water-ethanol (1:1 (v:v)), there was added 0.5 ml of glacial acetic acid and heated under reflux. To the obtained solution, there were added 0.86 g of iron powder and 0.80 g (4.3 mmol) of 4-chloro-5-methyl-2-nitrophenol and the mixture was heated under reflux for additional 20 minutes. After cooling and adding 30 ml of acetone, the iron powder was filtered and washed with 50 ml of acetone. The filtrate was combined with the washing liquor and the solvent was distilled off therefrom under reduced pressure to thereby give a brown solid. The obtained product was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 200 g; eluent: hexane-ethyl acetate (2:1 (v:v)). The solvent was distilled off from the 1,100-2,000 ml fraction and thus 0.29 g (1.8 mmol) of 2-amino-4-chloro-5-methylphenol was obtained as yellow crystals. The yield was 43%.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 20 minutes
  5. temperatureAfter cooling
  6. filtrationthe iron powder was filtered
  7. washwashed with 50 ml of acetone
  8. distillationthe solvent was distilled off
  9. customunder reduced pressure to thereby give a brown solid
  10. distillationThe solvent was distilled off from the 1,100-2,000 ml fraction

Sources & evidence

ORD record
ord-824bf2c04d4744498005c5a39b8aa75e
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Linked notes

Loading…