3-Nitrophenol → 2-[(3-Nitrophenoxy)methyl]furan

HRID 1964050Notes

Reaction equation

HRID 1964050 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]1[O:14][CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 2195202-(Chloromethyl)furan

Product 1

HCID 668768842-[(3-Nitrophenoxy)methyl]furanYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

20 mL of DMF was blended with 2.0 g (14.4 mmol) of 3-nitrophenol, 3.57 g (30.6 mmol) of 2-(chloromethyl)furan, and 2.0 g (14.4 mmol) of potassium carbonate, and the mixture was stirred at 80° C. for 3 hours. After cooling the reaction solution to room temperature, the reaction solution was extracted with ethyl acetate, and resultant solid material was washed with water 3 times and with a saturated sodium chloride solution, and dried over magnesium sulfate. Thereafter, filtration was conducted and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give 2-[(3-nitrophenoxy)methyl]furan (yield: 91%).

Workup

  1. temperatureAfter cooling the reaction solution to room temperature
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washresultant solid material was washed with water 3 times and with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThereafter, filtration
  6. customcondensed
  7. customThe resulting crude product was separated
  8. custompurified

Sources & evidence

ORD record
ord-c114bb97c47a4c819e649d7bbee6a751
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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