Sodium Thiosulfate → 2-Amino-4-ethylphenol

HRID 2056108Notes

Reaction equation

HRID 2056108 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1)[CH3:2].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[NH2:10][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

5

Reactant 2

HCID 24477Sodium ThiosulfateHCID 919014-Ethyl-2-nitrophenol

Product 1

HCID 7218852-Amino-4-ethylphenolYield 18.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-ethyl-2-nitrophenol (5.5 g, 0.032 mol) in ethanol (180 mL) and water (90 mL) was added sodium thiosulfate (23 g, 0.131 mol) at room temperature. The heterogeneous mixture was stirred at 80° C. under an atmosphere of nitrogen for 16 hour. The reaction mixture was cooled to room temperature, and ethanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3×100 mL), and the organic layer was washed with brine and dried under sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica using 0%-25% methanol/dichloromethane as a mobile phase (×2). The solvent was removed under reduced pressure to give 2-amino-4-ethylphenol (0.89 g, 0.006 mol). 1H NMR (DMSO-d6, 400 MHz) δ 8.61 (br, 2H), 6.47 (d, 1H), 6.37 (s, 1H), 6.18 (d, 1H), 2.17 (q, 2H), 1.08 (t, 3H). MS: MH−: 137

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customethanol was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  4. washthe organic layer was washed with brine
  5. customdried under sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash column chromatography on silica using 0%-25% methanol/dichloromethane as a mobile phase (×2)
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7739ea03889540d9acb3fa716f3e627c
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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