Sodium Carbonate → HCID 66664995, compound

HRID 607259Notes

Reaction equation

HRID 607259 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[Fe]>[NH2:16][C:4]1[CH:3]=[C:2]([Cl:1])[CH:15]=[CH:14][C:5]=1[O:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 129406294-(4-Chloro-2-nitrophenoxy)phenol

Product 1

HCID 66664995HCID 66664995, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product of Example 151A (400 mg, 1.506 mmol) and iron powder (336 mg, 6.02 mmol) in acetic acid (10 mL) and ethanol (10 mL) was heated at reflux under a nitrogen atmosphere for 25 minutes. The reaction was cooled to room temperature, diluted with water (50 mL), and treated with solid sodium carbonate until the pH was 6. Extracted with ethyl acetate (2×50 mL) and washed the organic with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. Co-evaporating the resulting oil with methylene chloride/hexanes provided the title compound as a tan solid (355 mg, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 25 minutes
  3. extractionExtracted with ethyl acetate (2×50 mL)
  4. washwashed the organic with brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation under vacuum
  8. customCo-evaporating the resulting oil with methylene chloride/hexanes

Sources & evidence

ORD record
ord-95cd7d7e354b442ab3cfbfedd8c542e4
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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