Sodium Carbonate → 4-(Benzyloxy)-3-methoxyaniline

HRID 1822827Notes

Reaction equation

HRID 1822827 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 217867071-(Benzyloxy)-2-methoxy-4-nitrobenzene

Product 1

HCID 272264-(Benzyloxy)-3-methoxyanilineYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 1-(Benzyloxy)-2-methoxy-4-nitrobenzene (26 g, 100 mmol) dissolved in ethanol (500 ml) in a 2 liter one-neck flask was added dropwise under 30 minutes a solution af sodium dithionite in water (500 ml), stirring was continued at ambient temperature for 2 h and after that the reaction mixture was heated at 70–80° C. for approx. 4 h, cooled and alkalized with sodium carbonate. The precipitate was filtered, washed with water and dried. The combined water phases were extracted with ethylacetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The residue was combined with the filtered precipitate to afford 9.3 g (41% yield) of the product.

Workup

  1. temperatureafter that the reaction mixture was heated at 70–80° C. for approx. 4 h
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. extractionThe combined water phases were extracted with ethylacetate
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-331e4547bf0541bc80f4f4cd3ad71aa6
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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