Ethyl Acetate → 3-(Benzyloxy)-4-methoxyaniline

HRID 8207

Reaction equation

HRID 8207 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>O.C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 53140362-(Benzyloxy)-1-methoxy-4-nitrobenzeneHCID 43835034Tin dichloride dihydrate

Product 1

HCID 125477223-(Benzyloxy)-4-methoxyaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(benzyloxy)-1-methoxy-4-nitrobenzene (35.35 g, 136 mmol) in 1:1 ethyl acetate: ethanol (640 mL) at 80° C. is added tin(II) chloride hydrate in portions over 25 minutes. The mixture is heated at this temperature for 5 h. The mixture is allowed to cool to room temperature and stirred for 2 days. The mixture is poured into water (1 L) and neutralized with solid sodium bicarbonate. The mixture is extracted three times with ethyl acetate. The combined organic extracts are washed with water and brine, dried (sodium sulfate), filtered and evaporated to yield the title compound as a dark brown oil.

Workup

  1. temperatureThe mixture is heated at this temperature for 5 h
  2. extractionThe mixture is extracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1453f3f499cc49b1ac8cfe210902109d
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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