Tin chloride monohydrate → 4-(3-Ethoxyphenoxy)aniline

HRID 1505301Notes

Reaction equation

HRID 1505301 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:5]=1)[CH3:2].O.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 45051637Tin chloride monohydrateHCID 672349961-Ethoxy-3-(4-nitrophenoxy)benzene2×

Product 1

HCID 261897424-(3-Ethoxyphenoxy)anilineYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1-(ethyloxy)-3-[(4-nitrophenyl)oxy]benzene (Intermediate 3, 4 g) and tin chloride monohydrate (28.8 g, 139 mmol) in ethyl acetate (200 mL) was heated at reflux overnight (15 hours). The reaction mixture was cooled down. It was then diluted with ethyl acetate (50 mL), washed with saturated NaHCO3 (100 mL), brine (100 mL) and dried over sodium sulphate. After evaporation of the volatiles, the residue was purified by an SCX (wash of the column with methanol, adsorption of the compound, wash with methanol (3CV), desorption with 2N methanolic ammonia (3CV)). Evaporation afforded the title compound (2.9 g).

Workup

  1. temperatureat reflux overnight (15 hours)
  2. temperatureThe reaction mixture was cooled down
  3. washwashed with saturated NaHCO3 (100 mL), brine (100 mL)
  4. dry with materialdried over sodium sulphate
  5. customAfter evaporation of the volatiles
  6. customthe residue was purified by an SCX (
  7. washwash of the column with methanol, adsorption of the compound
  8. washwash with methanol (3CV), desorption with 2N methanolic ammonia (3CV))
  9. customEvaporation

Sources & evidence

ORD record
ord-ac580f2125ec4d949ff51a4ec1a42c7d
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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