Phenol → HCID 8714478, compound

HRID 2170228Notes

Reaction equation

HRID 2170228 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(OCC)(=O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH:6]=1)[CH:4]=[O:5])([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27347702-Fluoro-5-nitrobenzaldehyde

Product 1

HCID 8714478HCID 8714478, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-fluoro-5-nitrobenzaldehyde (1.0 g, 5.91 mmol), phenol (0.557 g, 5.91 mmol), and K2CO3 (1.635 g, 11.83 mmol) in dioxane (6 mL) was heated at 70° C. overnight. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (60 mL). The solution was washed with water (2×30 mL) and saturated aqueous sodium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give the title compound (1.43 g, 99% yield).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe solution was washed with water (2×30 mL) and saturated aqueous sodium chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-316bfceee45649a8bdac23d2da298cfa
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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