Phenol → 4-Phenoxybenzaldehyde

HRID 2360352Notes

Reaction equation

HRID 2360352 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:16]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 661394-Phenoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of p-fluorobenzaldehyde (1.6 mmol, 0.2 g) in dimethylformamide (8 mL) was added phenol (3.52 mmol, 0.33 g) and cesium carbonate (3.52 mmol, 1.15 g). The reaction mixture was headed to 90° C. for 3 hours at which time the reaction mixture was cooled to room temperature and filtered through a medium fritted funnel. The reaction mixture was then diluted with 125 mL of ethyl acetate and extracted with eight 15 mL portions of water followed by one 10 mL portion of brine. The organic layer was then dried with magnesium sulfate and evaporated to dryness. The title product was purified by column chromatography and 0.237 g (1.2 mmol) was recovered. 1H NMR (300 MHz, CDCl3) δ 9.91 (s, 1H), 8.02 (s, OH), 7.92-7.79 (m, 2H), 7.49-7.37 (m, 2H), 7.23 (t, J=8.0, 2H), 7.14-7.01 (m, 4H), 6.89 (t, J=8.3, 2H). 13C NMR (75 MHz, CDCl3) δ 191.28, 163.56, 156.41, 155.26, 132.28, 131.38, 130.41, 129.79, 125.23, 120.69, 120.45, 117.79, 115.61.

Workup

  1. filtrationfiltered through a medium fritted funnel
  2. additionThe reaction mixture was then diluted with 125 mL of ethyl acetate
  3. extractionextracted with eight 15 mL portions of water
  4. dry with materialThe organic layer was then dried with magnesium sulfate
  5. customevaporated to dryness
  6. customThe title product was purified by column chromatography and 0.237 g (1.2 mmol)
  7. customwas recovered

Sources & evidence

ORD record
ord-c41196c3cee84e2fbffe8b8ff30b5e75
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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